


Good to You

by QuidnamInferorum



Category: Supernatural
Genre: 1940s AU, AU, F/M, Fluff and Smut, Pianist!Dean, Smut, Swearing, and 40s slang, lots of swearing, singer!reader
Language: English
Status: In-Progress
Published: 2016-08-30
Updated: 2017-04-30
Packaged: 2018-08-11 18:30:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 26
Words: 42,000
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7903198
Author URL: https://archiveofourown.org/users/QuidnamInferorum/pseuds/QuidnamInferorum
Summary: <blockquote class="userstuff">
              <p>It's Chicago 1941, and the nightlife is booming. Roped into being the new singer at the club run by the mysterious Crowley, a young girl must face dealing with her past, escaping her present, and the fact that her pianist is stupidly hot. Inspired by a lot of things, but mostly the music video for "Good to You" by Marianas feat. Jessica Lee. Updated every other Sunday.</p>
            </blockquote>





	1. Prologue

Chicago has always been known for its nightlife. If you went downtown, the lights and sounds would draw you in, beckoning to you with the promise of cheap booze and easy women.

And, down one of thousands of alleys on one of thousands of streets, there was a bar. It was dark, it was secluded, and it was Crowley’s. Opened by Fergus MacLeod shortly after the end of Prohibition and named after himself, it had quickly become a staple of the Chicago nightlife. Sometimes, the line into the club would lead all the way back to the street, revealing the quasi-hidden gem to even more paying customers.

Inside the club itself was dark. With booths of a deep red that had high backs to give as much privacy to patrons as possible up against the dark walls. A single chandelier hung in the middle of the ceiling to shine a low light over the entire room, making the whole place feel intimate. A dance floor was towards the back of the club, next to a stage that had a phenomenal music act play live every night. Sometimes, the dancing would transfer to back rooms that were available for use to only some of Crowley’s most loyal and favored customers, where they were otherwise used for deals the employees knew better than to ask about.

Crowley’s employees were, as a whole, wholly unhappy to be there. They were paid well enough, sure, but none had chosen to work there. Each owed a debt to Crowley, for one reason or another, and they worked off their debt to him.

The main attractions, however, were the band. The stars of the band were the piano player and singer. The man who hunched every night over the piano was a tall man that could only be described as beautiful. His dirty blonde hair was slicked back just for performances and left wild every other time. His green eyes scanned the room every time he entered, trained to look for threats and hasty exits. Except during performances. Then they bounced between his fingers dancing across the keys and his partner.

She was the newest to fall into Crowley’s trap. She was to replace the previous singer after she disappeared about a month prior. After a stacked deal with the man himself, she found herself walking into the secluded club on a crisp March morning.


	2. Chapter 1

She pulled her coat tighter around her, fighting against the biting winds. Her short heels clacked against the pavement as she cursed herself.

Of course she had to make a deal with Crowley.

Of course she had to go work for him to pay off her debt.

Of course he’d ask her to come in her first day at a godforsaken hour.

She pulled out the scrap of paper she’d written the address of the bar down on, checking it for the third time in about a minute, trying to make sure that she wasn’t lost.

Y/N finally found the alley she was looking for, tucked away by a few legitimate businesses. She walked between the two buildings, the wind getting a bit stronger in the enclosed space. She turned the corner and saw the front of a beautiful nightclub. The name was written in elegant script above the black awning that covered a deep red door.

She walked up and rapped her knuckles thrice on the door. It took a moment before she heard it click open and was faced with the bouncer. A wide-set man made almost entirely of muscle appeared on the other side of the door. He smiled warmly at her, which struck her as odd for a bouncer.

“Hey, you must be the new girl,” his voice was coated with a Southern accent and smooth like honey. A part of her melted a little.

She nodded. “Yeah, that’s me. Name’s Y/N.” With that, she stuck out her hand.

His monstrous hand engulfed hers in a tight grip, and she prayed she wouldn’t bruise. “Nice to meet ya. I’m Benny. I work the door. Come on it, it must be freezin’ out there.”

“Thanks,” she mumbled, hurrying through the door the moment he stepped to the side.

“Can I take your coat?”

Y/N nodded once more. “Thanks.” She shrugged it off her shoulders and handed the coat to him. He laid it over the coat check counter before saying, “Follow me, Miss Y/N.”

She followed him through a short hallway that opened up into a beautiful, cavernous room. Her Y/E/C eyes scanned the room, trying to take it all in. She was slightly dazzled by the sight and, had it been a reasonable hour and had she been there to enjoy it, she would love to come here.

However, it was all tinted with the fact that she was forced into this position, which ruined the atmosphere for her a bit.

Benny and his kindness, however, gave her a bit of hope. Sure, everyone and their mother knew that Crowley was a bastard, but maybe her co-workers would be alright.

“Well, this is the main room. You’ll be performin’ up on that stage over there,” he motioned, rather pointlessly, to the large stage towards the back of the room. “Behind the stage are a few dressing rooms and a few private rooms for select patrons.”

Y/N flushed a little at that, but didn’t let her voice waver. “Select patrons?”

Benny sighed. “Trust me, the less you know, the better.”

She nodded. “Sounds about right.”

He gave her a sweet smile at that before continuing with his semi-tour. “That over there’s the bar. Cas runs it, but he ain’t in yet. Meg comes in about nine—oh, she’s the head waitress. She knows the other girls’ names better ‘an I do, so I’ll have her introduce them all.”

“What about the rest of the band?”

Benny cocked a thumb back towards the stage. “They should be back in their dressing room, but Gabe probably won’t show up until show time.”

“Wait, what?” she huffed. She had to be here at the crack of dawn, and one of her bandmates couldn’t bother to show?!

Benny laughed at her reaction. “Yeah, Gabe takes some gettin’ used to, but he’s a good guy. Don’t worry. Never heard someone make a sax sing like he does and he knows what he’s doin’. Dean’ll get you set up.”

“And Dean is?”

“The best damn pianist in town.” His chest puffed with pride. Obviously, they were friends. “Head on back, he should be waitin’ for you.”

Y/N smiled and nodded. “Thanks, Benny.”

“Anytime, Miss Y/N.”

“Ya know, just Y/N’s fine.”

“Whatever you say, Miss Y/N.”

She sighed in an exaggerated manner at that, which made him laugh a bit as he headed back to his post.

Standing alone in the giant room, she felt a little more lonely without the boisterous presence of the Southern gentleman beside her. Her footsteps and her breathing were the only sounds in the room, and all it did was make her feel even more insignificant.

She walked through a door marked “Employees Only” and was met with a dark hallway filled end to end with exposed brickwork. She had to take a moment, but she quickly found what she was looking for to her right, back behind the stage.

She opened another door and was met with a mid-sized room filled with a few dressing tables, instruments, and racks of costumes.

What immediately caught her eye, though, was the man sitting on the other side of the room. His short, dirty blonde hair was sticking up at every angle, as though he’d been running his large hands through it. His broad back and wide shoulders were hunched over a small table where his pen flew across a scrap of paper.

He didn’t seem to hear her enter, so she cleared her throat. “Um, hello?”

He started, obviously caught off guard, before turning around.

Of course he just had to be the most stunning man she’d ever seen.

He had a strong, straight nose the led to the most luscious lips she’d ever seen. With a square jaw and cheekbones sharp enough to cut with, she thought that he was perfect. Then she looked into his eyes. They were a shade of green she’d never seen before, and they were intoxicating.

He cocked a stupidly perfect eyebrow at her and asked, “Who’re you?”

She squared her shoulders a bit, forcing herself to get it together, before she answered. “I’m Y/N Y/L/N, the new singer.”

He frowned for a moment before realization dawned on him. “Shit, is it the twelfth already?”

She chuckled at that. “Yup, came after the eleventh like always.”

He grinned at that. Damn, even his teeth were perfect. “I don’t think a dame like you is gonna have any problems fittin’ in around here.”

She smiled at that, a genuine, excited smile. “So, Benny says you work the ivories?”

“I do,” he nodded. “Better than anyone else—”

“In town. So he said,” she finished.

He narrowed his eyes at her playfully, which made her smile even bigger. “Well, since you seem to know all about me already, maybe you can tell me somethin’ ‘bout yourself?”

“I’m really not at all interesting.”

“I disagree.”

She straight up flushed at that, not prepared for the sudden compliment. Were they flirting? Is that what she was doing?

She frowned, her brows furrowing together. “S-So, you working on something for tonight?” she stuttered out, ignoring the blush beginning to make its home on her cheeks.

He glanced back at his makeshift desk. “Yeah, I guess. Honestly, it’s not goin’ all that well.”

“Let me see it.”

His eyebrows rose at that, but he handed it over with no fuss.

“You a songwriter, too?”

“Oh, _hell_ no. I was just makin’ some changes so we could work it without one of us. Y’know, just in case.”

“You’re…you’re trying to take out the drums?”

“You’ll meet Gabe later, and you’ll understand.”

She giggled at that, and he smiled. “Everyone keeps warning me about him. I’m getting worried.”

“Ah, he’s harmless. Mostly. We just rag on him,” Dean smiled. “C’mon, let’s go see what ya got.”

“I’m sorry, what?”

He laughed. “I wanna hear ya sing, doll.”

She nodded, trying fruitlessly to hide her darkening cheeks. “Oh…that’s alright, then.”

“Should hope so. Then again, I’d always love to see what you’re made of, if you’re willin’ to share, doll,” he winked.

“You should be so lucky,” she snarked back without thinking.

He was grinning like a child on Christmas morning as they walked to the stage. Dean cracked his fingers, probably readying them for playing.

Once they got to the stage, he held out his hand to help her up. She knew she shouldn’t. She was already enjoying his company too much. Touching him might actually, physically break her. However, as she thought this all through, she reached her hand out to take his out of instinct.

Her smooth hand slid into his calloused ones, creating a wonderful contrast. As reticent as she had been to take it in the first place, she now found herself unwilling to return his hand to him.

They didn’t separate until he walked up to the piano. He let go as he sat himself down, using his now-free hand to motion to the mic set up next to him. It was set up so that his back wasn’t to it, so that he could watch the singer throughout the entire performance.

She sucked in a deep breath, preparing herself. “I’ve not had time to warm up, just so you know.”

He shrugged. “Let’s see how much you need it.”

“Just wanna warn you, that’s all.” She mumbled, stepping up to the microphone. She ran a hand over it, the cool metal circle trying to wipe away the warmth that Dean’s hand had given her. “Got a song in mind?”

He grinned. “Didn’t know ya took requests.”

“There’s a lot you don’t know about me.” She had meant for it to come out seductively, but it instead came out rather sad.

If Dean picked up on it, he didn’t let it show. “Well, then how about somethin’ slow? Mood music, y’know?”

She nodded. “I got one.”

He bowed his head slightly and moved his hand outward in a grand gesture, like he was asking her to walk through the door before him. “Whenever you’re ready, sweetheart.”

She took the microphone in her hands, smiling slightly to herself. She took a deep breath and began singing.

She had to be loud, as the microphone wasn’t on yet, but she felt more comfortable singing with it in her hands. It made her feel like a real singer, not some imposter who’d been forced into the job.

She chose a slow bittersweet ballad. It was one she had loved a child and that had played often on the radio in the orphanage. If she woke up tomorrow deaf, dumb, and blind, and she’d still be able to sing this song. Her voice crooned the words out, filling the empty room and echoing back slightly.

When she finished and silence returned, she turned to the pianist.

The cool, confident pose he had taken when first sitting down was replaced a hunched over version of himself. His elbows were resting on his knees with his fingers interlaced. Dean was looked up at her like he was seeing a miracle.

Before either of them could say anything, the sound of slow clapping filled the room. They turned towards the main entrance, where the source was standing.

In a crisp, perfectly tailored and undoubtedly expensive suit, stood the owner of Crowley’s. He was just a bit shorter than the six foot two Dean, with short brown hair and a matching beard. His default expression seemed to be smug, and his brown eyes sparkled with something akin to mischief.

His clapping stopped and his heads took their place in his pants pockets. “Fabulous, darling. Absolutely fabulous.”

As Crowley began walking towards the stage, Dean stood slowly and situated himself between her and their boss.

Crowley seemed amused by this. “Oh, come on, Dean. What do you think I’m going to do?”

Dean’s jaw clenched slightly, but he stepped to the side just a bit. He wasn’t standing between the singer and the owner anymore, but he was still close enough to jump in if needed.

Crowley smirked, but chose not to comment. “It’s lovely to see you again, my dear.” He took her hand and kissed the back of her knuckles.

She tried not to let her nervousness show, squaring her shoulders and standing tall. “Pleasure’s all mine, Mr. Crowley.”

He let her hand go and she resisted the urge to wipe it on her skirt. “I doubt that, darling. I see you’ve already got Dean here wrapped around your finger. I can’t wait to see you perform tonight.”

“Tonight?” Dean frowned. “That won’t be enough time for us to practice, get a good set ready.”

“I prefer to learn by doing, don’t you, Miss Y/L/N?”

Y/N swallowed, her throat suddenly dry. “Whatever you say, Mr. Crowley.”

“Exactly. Listen to her, Dean-o—she already knows the rules better than you.”

Dean’s jaw clenched. Without thinking about it, Y/N took hold of Dean’s arm, placing one hand on his bicep and the other taking his hand in hers. He relaxed minutely. “I promise, Mr. Crowley, we’ll do the best we can.”

“I’d appreciate it if you could do the best of someone better.”

She practically felt Dean’s anger rolling off of him, and she squeezed his hand just slightly. She prayed she was helping. “We will.”

Crowley smiled. “Wonderful. Can’t wait.”

And, with that, he turned on his heel and walked off the stage, heading towards the back. Even after he had disappeared backstage, Y/N and Dean remained silent a few moments longer.

“Sweetheart,” Dean began quietly and seriously. “I’m flattered, but I can’t play like this.” He grinned lasciviously.

That was the moment Y/N realized that she was still holding onto Dean. She jumped back, practically landing on the other side of the stage. “I-I’m so sorry! I wasn’t think—!”

He laughed, and it was as though Crowley had never come in the room to begin with. “Don’t worry about it, doll.”

Y/N smiled warmly, happy to see the original Dean make a comeback. “Well, good. Then we can start getting ready.”

“Much as we can with half the band missing.” He grumbled, sitting back down on his bench.

“I think we can handle it, don’t you?”

He looked up at her and smiled softly. “Yeah, I do, actually.”

She smiled, clapping her hands together. “Let’s get started, then!”


	3. Chapter 2

The next few hours were spent pouring over every music sheet in the building. Dean had Y/N sing a few more songs in a few different styles, claiming he needed to know what best suited her voice. She was suspicious, but said nothing.

By noon, the bartender, Castiel, entered with Meg. She was wrapped around him like vines on a house, but they separated when they saw that they weren’t alone.

Dean had shouted across the room that the private rooms were in the back, and Meg had sent him a glare that, for all intents and purposes, should’ve killed him.

Meg disappeared into the kitchen behind the bar, whilst Castiel took his post and began prepping for the evening.

Around two, Dean decided that it was time to take a break and give Y/N’s voice a rest. “Plus, it gives me an excuse to buy you a drink!” he’d winked.

“Well, I’m not one to turn down a free drink!” Y/N smiled, already enjoying this day a thousand times more than she thought she would.

He held out his hand to help her off the stage, and she took it, both of them ignoring that she didn’t need the help and the fact that there were stairs off to the side to make for easy access.

They walked up to the bar, and Castiel smiled. “Good afternoon, Dean.” He bowed his head slightly.

“Heya, Cas. This here’s Y/N Y/L/N, the new singer.”

“I assumed as much.” Castiel turned to her. “It’s a pleasure to meet you, Miss Y/L/N.”

“Please, just Y/N’s fine.”

“If you insist. I am Castiel Novak.”

“You can call him Cas,” Dean finally took a seat on one of the stools.

The second Dean sat, Castiel began pouring a shot of whiskey for the pianist. Dean downed it all in one go before putting it back down on the bar. That was apparently Castiel’s signal to refill, as that’s what he did next. Dean turned to Y/N before motioning to Castiel with his head. “What about you, doll?”

Y/N frowned. “I can’t have anything too strong, unfortunately. How ‘bout a Shirley Temple?”

“You a lightweight?”

Y/N laughed, but Castiel answered. “It’s not good for her voice, Dean.”

Dean’s ears tinged a little pink. “I-I knew that, Cas. Jus’ askin’ a question, that’s all.”

She sat down next to her bandmate as the bartender slid her drink to her. “Thank you, Castiel.”

“You can call him Cas.”

“When he says I can, Dean.”

“I do not mind, Y/N. Whichever you prefer is fine with me.”

She huffed. “Well, if you’re sure it’s okay.”

He shrugged, pouring another shot for Dean.

“Alright, well then, thank you, Cas,” Y/N smiled.

That was the moment Meg walked out of the kitchen, now in a white shirt and black skirt that were barely appropriate that Y/N had to assume was her uniform. Her brown hair was swept back beautifully, framing her face, but keeping it out of her way. Her chocolate eyes landed on the three at the bar, and her perfect lips pulled back in a smile. “Howdy folks!”

Castiel smiled softly at her, whilst Dean raised his drink towards her. “Meg, Y/N. Y/N, Meg.” He said in the way of introduction.

“Ah, new singer, right?”

Y/N stood and held out her hand to the new girl in the room. “That’s right. And you’re the head waitress, right?”

“That’s right,” Meg nodded and shook Y/N’s hand firmly. “Don’t worry about meetin’ the other girls. They come and go so fast, even I can’t keep track of ‘em all.”

Y/N’s eyebrows shot up at that. “Wow…how do you get anything done then?”

“No clue,” Meg grinned.

Y/N chuckled in disbelief at that. “Well, I can’t wait to see how you do it.”

Meg grinned, heading behind the bar. “Same here. Cas and I heard you both a bit when we came in, but I’d like the full effect.” She walked over, placed a quick kiss on Castiel’s cheek, then leaned over and placed her hand over Dean’s drink.

“Hey!”

“How many have you had, Dean-o?”

He grumbled, but Castiel answered. “That is his fourth shot.”

“Then less drinking, more practicing.”

The pianist grumbled, but stepped back from the bar. “Fine. C’mon, Y/N, let’s give ‘em a show.”

* * *

 

The day went by quickly as everyone else filed in. Chuck came in, introduced himself quickly, then reintroduced himself to the bar and Castiel.

After a drink, he was up on stage with them, fine tuning a few songs with them. He seemed a bit squirrely but otherwise rather nice. He was shorter than the other men in the club, with brown scruff to match his rather matted hair and tired eyes.

About an hour before opening, Gabriel swaggered in, his blonde hair half gelled back and half standing up at different ends with lipstick stains on his face and lapel. His hazel eyes shone with glee, seemingly proud of himself. He waved to Castiel, winked at a few of the waitresses, then made his way backstage, completely ignoring the new addition to the band.

Dean and Chuck seemed unsurprised by this, so Y/N said nothing.

When he finally came out, he smiled flirtatiously at the new singer. “Hola, mi amor.”

She didn’t even get a work out before Dean interrupted. “Don’t even think about, Gabe.”

Gabe threw a confused look at Dean, before grinning. “Ah. Okay. Read ya loud and clear.”

Dean glared at his bandmate, trying to hide the pink tinging the tips of his ears. Y/N bit her bottom lip, suddenly slightly more hopeful.

“C’mon, let’s get started, slackers!” Gabe grinned, taking a seat behind his drums and beginning to play.

Y/N’s eyes widened enough to nearly pop out of her head. He was amazing. He was mesmerizing. He threw himself fully into his music, the passion flowing out to touch everyone in the room. She couldn’t hear anything except his playing, and she wondered idly if that was because she was mesmerized, or if because everyone had stopped what they were doing to listen to him.

When he stopped a few moments later, he turned to Dean and said, “Ready?”

Dean chuckled. “As always.”

And, with that, they began their first full rehearsal.

* * *

 

The bar filled up within moments of it opening. The new band stood behind the stage, running through their final preparations before beginning their show for the night.

Meg had been lovely enough to pull Y/N aside about thirty minutes earlier and get her all spruced up. She had helped with her hair and they’d found an appropriate dress in the racks hidden away. It was elegant and hugged every curve of her body. It went all the way down to the floor, brushed against her feet in her shoes, the same shoes she’d worn to work earlier that day. Her Y/H/C hair was swept back and to the side, layering over her right shoulder. Meg might’ve gone a little overboard with the make-up, but she claimed that it would withstand the spotlight and that’s what mattered.

It was worth it, though, when the girls exited the dressing room, and the boys looked at Y/N like they’d not seen her before. Dean especially looked like someone had knocked the breath out of him.

Meg had nudged Y/N’s side, grinning. Y/N’s now-red lips split to smile widely at the head waitress. Meg had then accepted Y/N’s thanks and headed out to take care of patrons and the other girls.

The plan was for the boys to go up on stage before Y/N, then introduce the new singer to the crowd. Gabriel and Chuck had told her to break a leg, then headed out.

Dean’s large hand landed softly on her left shoulder, and she looked up into his soft green eyes. He smiled warmly. “You’re gonna knock ‘em dead, doll.”

Y/N nodded, refusing to let any nerves get to her. “I know.”

Dean laughed at that. “And so modest!”

She shrugged playfully. “I know what I got, Winchester.”

“Anytime you’re willin’ to share, doll, I’m all ears.”

She looked up at him, a comeback on the tip of her tongue. That comeback died, however, when she locked eyes with him. She had expected some mischief in his eyes, or a salacious smile gracing his cheeks, and, instead, she was met with a serious expression.

She gulped and tried to ignore her heart beating in her ears. After a moment, she managed to squeak out, “You’ll be the first to know, Dean.”

He gave a genuine smile at that before lightly patting her on the shoulder. “See ya out there, doll.” With that, he threw one last playful grin at her and headed out into the main room.

Y/N was left alone backstage. She heard the boys tuning their instruments once more mixed with the low murmur of the patrons as they filed and settled in for a night of fun.

“Nervous?”

Y/N nearly jumped out of her skin before she turned to see her new boss standing towards the end of the hall. She heard the click of his designer shoes as he slowly walked over to her. “There’s no reason to be nervous, darling.”

“I’ll be great, Mr. Crowley.”

His eyebrows raised slightly as he came to a stop beside her. “Good. That’s what I like to hear from my investments.”

Her jaw clenched, but she looked directly into his eyes. “I’ll be great, Mr. Crowley,” she said as evenly as she could, refusing to let him see her fear.

He smiled before turning on his heel and beginning to walk away. “Can’t wait.”

She breathed out a sigh of relief when he disappeared out into the main room. He hadn’t been listening to their rehearsing all day, locked away in his office, and now she was a bit more worried. If he didn’t like their performance, there went her freedom. Well, what little she had left. But the small amount of freedom Crowley offered her was better than nothing.

She heard Gabriel speaking now, thanking everyone for coming that night and promising them a wonderful time. Then, he introduced her.

“And tonight, you’re all in for a treat. We’ve got a special songbird that starts tonight, ready to knock your socks off. Please welcome the lovely, the melodious, the amazing Y/N Y/L/N!”

She took one last deep breath as the polite applause began, then opened the door to the main room.

It looked quite different than it did empty, which shouldn’t have surprised her as much as it did. The low light hid everyone’s faces, though, so she could only make out builds and some outfits. Tables were laid out around the room, each filled with a few people. The booths had some men sitting there with girls wearing outfits similar to Meg’s curled up at their sides.

Then, she looked to the stage, and she saw her bandmates. They were all smiling at her, and Dean was standing by the steps, his hand out and ready for hers.

She took it happily, relishing in the warm of the contact, before walking up the steps as the applause began dying down.

The spotlight and floor lights eliminated her ability to see even the outlines of the audience, which made her feel better.

She turned to throw one last look at her pianist, who winked at her, then began playing.


	4. Chapter 3

It felt like a strange mixture of forever and no time at all before they were finished for the night.

They’d begun with a slow song, as everyone settled in. Then, they’d spiced it up with some fast songs, to encourage dancing. They’d played rather fast jazz for most of the set, barely giving any of them time to breathe.

The band, as a whole, was amazing. They left the stage together, leaving a thunderous applause behind them. They walked backstage, the boys laughing. Y/N watched with a big smile on her face. Finally, Gabriel turned around and threw an arm around her shoulder.

“You gotta let me buy ya a drink, sweetheart! You killed them out there!” He grinned, pulling her close.

She laughed, ducking out of his grip. “Not a chance, Gabe.”

“You’re breakin’ my heart, doll!” Gabe gripped his shirt where it rest over his heart, pretending to be in great pain.

Dean threw his arm around her now, pulling her as close to him as he could. “I’m sorry, Gabe, but she’s made her choice.”

Gabriel gasped dramatically. “What? You chose _him_ over _me_? I thought we had something special!”

Y/N laughed and twined her arms around Dean. “I’m sorry, Gabe. I tried to fight it, but I just couldn’t,” she answered him as dramatically as possible.

Chuck laughed. “I didn’t know Joan Fontaine was our singer tonight!”

They all laughed at that. Chuck gave her a genuine smile. “In all seriousness, Y/N, you were amazing.”

“Yeah,” Dean began, squeezing her slightly. “We’re happy to have you with us, doll.”

“Yeah, anything to distract from their ugly mugs,” Gabriel joked. Chuck glared at him playfully.

“Well,” Y/N began. “I think it’s all because you guys are so easy to work with.”

Dean shook his head. “Nah, it’s all you.”

She smiled brightly up at him. “Well, then, at the very least, I couldn’t’ve done it without you, so, thanks.”

He shrugged. “Probably not.”

She shoved him, moving out of his arms as she laughed. “Glad you’re a better piano player than comedian!”

Dean grinned. “I’m even better at other things, doll!”

“Ugh, the private rooms are back there. Get it out of your system,” Chuck rolled his eyes.

They all laughed at that. It was then that Chuck bid farewell, saying he had an appointment with Mistress Magda (Y/N was afraid to ask) that he couldn’t miss. Gabriel then took the opportunity to go flirt with some dame at the bar he’d been eyeing all night.

Y/N and Dean, however, decided to call it a night.

“Please tell me we don’t have to be here as early tomorrow,” she begged.

“Nah, that was just Crowley wanting you to have prep time.”

His name made Y/N’s steps stop. “Do…do you think I did well enough?”

Dean turned to her, slowing to a stop himself. “If you did any better, I think their hearts woulda exploded.”

She nodded, her brow still furrowed. “So…do you think…do you think _he’ll_ be happy?”

She nearly jumped out of her skin when Dean’s hands landed on her shoulders. “The fact that you ain’t seen him since the show started is a good sign, Y/N. Trust me, the less you see of him, the better.”

She gave him a half-hearted smile. “If you say so.”

“I do. Now, get your pretty ass outta that gown. I wanna go home.”

“You don’t need to wait on me for that, Dean. Go, I’ll be fine.”

“I ain’t lettin’ you walk home alone, sweetheart.”

She frowned. “You don’t even know where I live. What if I’m on the other side of town?”

He shrugged. “I ain’t lettin’ you walk home alone.”

She took a moment to look at him, searching him for any hidden agendas.

He was standing there, his hand scratching the back of his neck, the tips of his ears beginning to pinken. He shifted slightly in his place as well, exuding a nervous energy.

She placed her hands on his shoulders, pulling him down closer to his level. She leaned up and placed a soft, quick kiss on his cheek. She fell back on the back of her feet and smiled. “I’ll be quick.”

He looked a little stunned as she turned on her heel and walked into the dressing room. She could only hope that he didn’t notice her cheeks beginning to match her dress.

* * *

Thankfully, it turned out that they were at least in the same direction. Y/N was currently in a hotel about ten miles south of the club, and Dean’s apartment was only a few miles beyond that.

They walked into the parking lot and Dean placed his hand on the small of her back before pointing. “That’s my Baby there.”

She was a beautiful car. Obviously well-maintained and somehow shining under the low street lights, sat a sleek black Chevrolet. Y/N would be lying if she said she knew the make and model, but even she knew that it was special. Even if the only thing that made it special was the complete adoration it was shown by its owner.

“She’s absolutely tops, Dean,” she breathed out, smiling up at her chauffeur for the evening.

His smile looked like one of a kid on Christmas morning. “Well, c’mon, I’ll introduce ya.” His hand left the small of her back. Instead, he held out his arm for her to take.

She twined her arms in his and said, “Can’t wait!”

He let her into the vehicle, and the smooth leather interior was one of the most luxurious things she’d ever felt. “Jeepers, Dean…how’d you afford this?”

Dean climbed into the driver’s seat, shifting the bench seating slightly. “Well, it was my dad’s. He was a mechanic, and he bought it offa some guy when it was a wreck, then restored it. Taught me everything I know ‘bout cars while he did it, too.” he glowed slowly.

Y/N’s fingers trailed over the seats, her eyes watching it give just slightly under her touch. “That’s amazin’, Dean. I’m kind of jealous.”

Dean started up the car and pulled out of the parking lot quickly. “Really?”

“Yeah. Musta been nice,” she answered absentmindedly.

“Well, sure learned a lot from the old man,” Dean shrugged, focusing on driving.

They sat in a comfortable silence after that. Y/N watched the lights flash by, and Dean focused on his driving. The only breaks were when Y/N gave him directions, pointing around corners and down side streets.

Finally, they pulled up to the dingy motel. It was barely standing and, when she had first checked in, she worried that it was abandoned.

She crawled out of the car herself, waving off his offer to get the door for her. She turned around, leaning against the window. She smiled at Dean warmly and thanked him once more for the ride “home.”

He was frowning, his eyes inspecting the crappy motel and obviously finding it wanting. “You sure you’ll be okay here?”

She shrugged. “For what I’m payin’, I can’t even be sure there’s a bed in there.”

His brow furrowed even more.

“I’ll be fine, Dean. You’re sweet to worry,” she smiled.

There was a beat of silence before he spoke again, “Can I pick you up in the morning?”

She sighed. “Dean…”

“Look, please? At least I’ll know you’re alive, and you aren’t even outta the way, alright?”

She chewed on the inside of her cheek, thinking it over. She would like to keep her one pair of shoes alive long enough to get her until her next paycheck, and walking twenty miles back and forth every day was not conducive to that.

Honestly, though, that was just an excuse. She just wanted to spend more time with Dean.

So, finally, she shrugged. “Alright, if you insist. What time do you usually go in?”

He visibly relaxed a little at the promise. “I’ll be by around 12, if you’re good with that.”

“See ya then,” she patted the door before pushing herself off of it and turning around. She’d only gotten a few feet, however, when she heard Dean call her name out once more.

She turned back around, her eyebrows raised.

He answered her confusion with a soft, genuine smile. “Sweet dreams, doll.”

She gave him one of her own. “Good night, Dean.”

With that, he drove off, and she walked into her shitty little motel room. She shut the door behind her, locking it, then got ready for bed and crawled under the scratchy blankets onto the lumpy mattress. However, she felt almost none of those things, just eh warmth his smile had given her.

Maybe this job would turn out better than she expected. 


	5. Chapter 4

“So, why did I see Dean and you comin’ in together?”

Y/N turned to see Meg suddenly behind her. They had been in the store for a good hour by this point, looking for shoes for the new singer to wear during performances. Meg had used an interesting choice of words to describe why Y/N’s barely-held-together loafers weren’t acceptable, and, shortly after entering, Y/N had gone looking for a new pair of loafers, whilst the waitress had thrown her arms up in defeat and gone to get the singer some new shoes.

It had been about two weeks since the new singer had joined Crowley’s crew. Honestly, as much as Y/N was afraid of Crowley, and as much as he sucked the life and air out of room whenever he was around, the rest of the team had welcomed her with open arms.

Especially Dean.

They spent almost every moment together, what with the daily rides to and from her crappy motel room to the club. Then, once inside the club, she spent most of her time with the boys.

So far, Chuck had been nothing but nice, if a little neurotic, to her. She’d seen him lose him temper once or twice, which had been scary, but nothing too major. As long as he met with his Mistress Magda away from her, she had enjoyed her time with the man.

Gabe was harmless, all in all. He flirted with her, but he would easily find himself in another’s arms by the end of the night. Dean sometimes gave him shit when he felt the flirting went too far, but, otherwise, he and Y/N were good friends.

Dean, however, was an entirely different story. He and Y/N were practically attached at the hip, often times no more than ten feet away from each other. The two would flirt, they would laugh, and usually found some seemingly innocuous reason to touch each other in practically innocent ways.

Today, though, was a girl’s day. After her performance last night, Crowley had come out and given her a hard time about her terrible loafers under his beautiful dresses. He’d sent the two girls to the store and told them to bring back something acceptable, telling them to just put it on his account.

So, now here they were.

“What?”

“You and Dean have been coming in together every day. Are you two—?”

“No!” she flushed. “No, nothing like that. He just…he just wants to make sure I’m safe, that’s all.”

Meg grinned. “Oh, if that’s all. Just wants to make sure _his girl_ is safe.”

Y/N huffed, glaring at the girl with her. “We’re not…we’re not going steady.”

Meg laughed. “Give Dean some time. He can be a bit thick.”

The singer giggled at that. “Well, he should move a bit more quickly, unless he wants Gabe to snatch me up.”

Meg threw her head back in laughter. “Please, like Gabe could concentrate on one girl long enough.”

“I guess I’ll have to settle for Dean, then,” Y/N sighed dramatically.

“Well, when you pick shoes like these,” Meg snatched the sensible in both looks and price loafers that Y/N had picked out. “How can he resist?”

Y/N took them back. “They’re fine.” she mumbled, holding them to her chest.

Meg sighed heavily. “Alright, well, we can go, then. I’ve got a few pairs for you that’ll match with your dresses.”

Y/N thanked her, and the two walked to the row of cashiers. Meg put the heels on Crowley’s account, practically whispering the name to the lady behind the counter, who blanched and nodded, scurrying away.

Y/N waited behind her coworker for the cashier to return. “Is everything okay?”

Meg shrugged. “Happens whenever we mention his name. She’ll be back in a minute.”

Y/N sighed. “How long does this usually take?” she asked as she watched the cashier talk to an older man, pointing back at them.

Meg frowned. “Not this long.” Her eyes narrowed as she watched the exchange. She seemed to tense a bit, and Y/N could begin to feel anxiety roll off of her companion.

“Meg? What’s wrong?”

“Shit.”

Before another word could be said, the cashier and the older man were back behind the counter. The girl gave them a strained smile and told them that the shoes had been credited to the aforementioned gentleman’s account.

The man however, had his brown eyes trained squarely on Y/N. She fidgeted slightly under her gaze. She suddenly felt Meg’s calloused hand grip her arm. When she turned to the waitress, she was wearing a tight smile. “Thanks, but we need to go now.”

“Meg, I’ve not bought my shoes yet.” Y/N frowned.

“Get them later,” she hissed to the singer.

“It’ll only take a second,” the older man said, his eyes not leaving Y/N.

The ends of Y/N’s fingers began to tingle as Meg’s grip started to cut off the blood to the rest of her arm. “Meg, my shoes are barely staying on my feet,” she practically whispered to her companion.

Meg turned to her, something akin to fear in her eyes. “Please, Y/N, get them later.”

The singer nodded slowly. “Al-Alright.”

The older man took that moment to speak. “Here, give us the shoes; we can hold them for you until you return.”

Y/N smiled graciously at the man as she used her free arm to hand him the shoes. “Thank you.”

“Yeah, yeah, thanks a lot. Let’s _go_ ,” Meg immediately began dragging her companion out of the department store before another word could be exchanged.

It wasn’t until they were halfway back to Crowley’s that they spoke. “Meg, think you can let go of my arm now?”

Meg dropped her arm like it had burned her, mumbling an apology under her breath. Then, she stopped in her tracks and thrust the bag of new shoes into Y/N’s arms. “Don’t mention that guy to anyone, got it?”

“That guy? You mean the manager?”

“Honey, he wasn’t the manager. He’s some copper that’s been chasin’ Crowley for as long as anyone can remember.”

Y/N gulped audibly.

“He’s bad news, alright? Don’t mention him to anyone, no matter what, got it?” Meg stared down the singer. “We can’t let it get back to Crowley.”

Y/N nodded. “Yeah, got it.”

Meg sighed heavily. “Sorry, I didn’t mean to scare ya.”

The singer shrugged, but said nothing. She knew that Meg was only trying worried, scared about keeping them both safe. Plus, with her own experience with the police, she wasn’t exactly chomping at the bit to jump into bed with them.

The girls walked back to the bar in silence, afraid to speak anymore on the subject.

* * *

 

It had been another fantastic show for the band. They were getting better and better with each show, and even Crowley had made an appearance during their performance (it had resulted in Y/N’s first false note of the night), but had disappeared before the end of their set. The boys promised that, had he been waiting for them in the back, _that_ would’ve been bad news.

Then came their nightly ritual: Chuck would go hit up Cas for another drink; Gabe would disappear into one of the private rooms with either a waitress, patron, or both; and Y/N and Dean would head off into the back to let her change out of her performance clothes.

When they met back up in the hallway, Dean frowned. “I thought you were getting new shoes today.”

“I did. Don’t you remember Chuck slapping Gabe over his comments about them earlier?”

“No, no, I mean, you still have your regular shoes. You were all excited to get new ones when you went out with Meg earlier. What happened?”

“I, uh, I forgot my purse when we went.”

Dean frowned and, for a moment, she was sure he had caught her in her pathetic lie. Instead, he responded with, “Well, why don’t I pick you up early tomorrow? We can go together, get you some new shoes.”

“Oh, Dean, you’re a real sweetheart, but—”

He shook his head, already moving towards the front of the club. “Doll, for as long as I’ve known you, you’ve been complaining about those shoes.”

“So, what, you saying you’re sick of hearing about it?”

He chuckled. “Obviously.”

They both gave a warm good night to Benny as they walked out—the boys even stopped to hug for a moment—and then were in the car, headed home.

When they arrived at Y/N’s motel, she took one step out of Dean’s car and nearly tripped over her own feet. She had taken a step, but the shoe of her left shoe had been left behind.

Once Dean had stopped laughing, he was adamant about getting her new loafers the next day. “And none of that malarkey about these shoes still being fine, got it?”

Y/N frowned, but still nodded.

“Alright, I’ll be by ‘bout 11, then, take you over to the store.”

“No!”

Dean started at that. There was no way he’d missed the panic in her voice or the way her hands were gripping the passenger side door hard enough to turn her knuckles white.

He spoke slowly but firmly, like she was a wild animal he was afraid of spooking. “Y/N, you gotta tell me what’s wrong.”

She sighed heavily. “I just…” she scrambled. “I just don’t want to bother you. I’ll just walk down myself in the morning.”

“You aren’t ever a bother, doll.” He spoke softly.

She frowned. Honestly, she knew she was just being paranoid. Meg had scared her with their talk earlier that morning, and she was taking out her fear on Dean now.

So, instead of fighting him again, she conceded, taking solace in the fact that she’d at least have Dean beside her.

He finally smiled at her with her concession, his shoulders relaxing slightly. Before he drove away, he wished her sweet dreams and only laughed a little bit when she began to walk away in her broken shoes.

* * *

 

Of course he’d pick this department store.

Y/N held her head in her hands, her elbows resting on knees. When Dean had asked, she had blamed the position on the fact that she was exhausted.

“You got me up so early, Dean!”

“Doll, you act like it’s dawn.”

“It is for us!”

“I apologize. Next time, I’ll give you a reason to be so tired.” He’d earned a smack on the arm for that retort.

However, he had picked her up at eleven, as he promised, and drove her to the same exact department store she’d visited with Meg the previous day.

It shouldn’t have surprised her really—where else did she think he was going to take her? _Not_ the biggest department store within twenty miles?

She thought hard. What were the chances that agent was still there? Even if he was, all she had to do was grab her shoes and get out. Just be quick, and everything would be fine.

He’d parked and began to get up and out before Y/N spoke up, “You know, you don’t have to come in with me, Dean.”

“Not a big deal.”

“I have some shoes I set aside yesterday, Dean, so I’ll only be a second.”

Dean frowned. “I can get a few things while we’re here, anyway.”

She sighed.

A twinkle entered Dean’s moss green eyes, and his stupidly perfect lips pulled back in a smirk. “Unless you’re gettin’ something _special_.”

“I don’t know what you mean.”

“Uh huh,” he nodded, the smirk getting bigger. “I bet. Just like you _definitely_ don’t know about the lovely lingerie section that is in this store.”

“Shut up,” she huffed, ignoring her growing blush and climbing out of the car herself. “Fine, go get whatever you’re buying, and I’ll meet you back here.”

“You sure you don’t want me with you? I mean, I’m kind of a connoisseur with ‘nighttime attire,’ and—!”

“I’ll see you later!” she said in an octave higher than usual as she scurried into the store, leaving a laughing pianist in her wake.

The store, shockingly, hadn’t changed much in the twenty four hours since Y/N had last visited. She found her way back to the women’s shoe section, searching around for anyone to help her.

She finally found someone who worked there, a petite brunette with big, brown puppy dog eyes. “Excuse me?”

The girl turned with a smile plastered all over her face. “Yes, ma’am? How can I help you?”

“Um, I was here yesterday, buying shoes and a pair was set aside for me to pick up.”

“Ah, alright, well, follow me,” the store worker began leading Y/N over to the cash registers. “Name, please?”

“Y/N Y/L/N.”

The girl looked around the area, her frown becoming deeper as she continued to find nothing. “I’m sorry, but I don’t have anything here.”

The singer furrowed her brow. What other name could—?

_Oh. Shit._

“Um,” she began, drawing the worker’s attention back to her. “It…It might be under another name.”

“Oh? Okay, well, what name, then?”

Y/N leaned in and whispered the name, “Crowley.”

The store attendant blanched, just as her coworker had done the day before. “O-Oh.”

The singer frowned. “Look, it won’t go on Crowley’s account, I’m paying for it myself, so if you just get me the shoes, we can get through this quick.”

The attendant fidgeted. “Well, I’m supposed to let the manager know—”

“ _Please_ , it won’t be on Crowley’s credit, and it’s only a pair of shoes. I’m begging you.”

“I can’t risk my job ju—”

“Don’t worry about it, Winnie, just ring her up.”

A large, calloused hand landed on the singer’s shoulder, and she froze. She turned slowly to see the older man from yesterday standing behind her, a stern look on his face. “I need to borrow the lady for a minute, so you can just ring her up.”

The girl—Winnie—nodded nervously and ran off to the back, probably to get the shoes.

Y/N’s hands began shaking, and she held her own hands to try and hide it from the officer. “Thanks for the help, but, I, uh, I really am in a rush, and—”

“Name’s Robert Singer. I’m a federal agent. Though, I’m guessin’ Meg told you that part.” he began.

She couldn’t look him in the eye, so she turned her head back to face the cash registers.

His hand tightened slightly. “We do know who you are, Miss Y/L/N. And we know how to came to work for Crowley.”

She stiffened at that.

“Now, I’m not here to bring you in. I can’t—Crowley made sure of that—but I just wanna talk.”

“I have someone waiting for me, Mr. Singer,” she began slowly, trying to keep her voice as even as possible.

There was a moment of silence, before he answered. “Well then, I ain’t got a lot of time. Listen, we’ve been trying to take down Crowley for a long time now, but we need one of you to help us.”

“No.”

“Please, you know how he works, Ms. Y/L/N.”

“And you know what’ll happen to me if I welsh on our deal.”

He chuckled a bit at that. “Ms. Y/L/N, you’re talkin’ to a federal agent. Don’t you think _I_ could get your charges dropped, too?”

The thought had crossed her mind. “I don’t think Crowley to be the kind of man who takes betrayal lightly, Mr. Singer.”

He sighed, the heavy breath brushing aside the loose hairs at the top of her neck. “Ms. Y/L/N, please. He can’t be left to do what he wants. Just, take my card and prom—”

They heard a throat clearing beside them, causing both heads to turn to the interruption. There stood Dean, with several new shirts draped over his left arm. His fists were clenched tight enough to whiten his knuckles, and he wore an uneasy expression on his face, like he wasn’t sure how to feel at the moment.

Mr. Singer sighed heavily. “She’s with you, I’m guessin’.”

Dean nodded curtly. “Yeah. Sorry, Bobby, love’d to chat, but we’re gonna be late. C’mon, doll.”

Y/N practically ran towards her pianist, taking his free hand in hers and squeezing it for dear life. He squeezed it back just a bit too hard, but she kept her flinch down.

Mr. Singer smiled sadly, but nodded. “Alright…Winnie, you can come out now.”

With that, the attendant seemingly materialized from thin air, holding the box of shoes. She looked down, refusing to make eye contact. Y/N paid for the shoes with only her free hand, which made the exchange all the more awkward.

The moment she held her new shoes in her hand, Dean was practically pulling her back towards the exit. As she struggled to keep pace with him, she prayed that this one moment wouldn’t ruin everything.


	6. Chapter 5

The easy talks and laughter that usually filled their rides together was instead replaced with awkward silence.

Y/N pretended to be occupied by putting on her new loafers.

Dean pretended that he was incredibly focused on driving.

She needed to explain herself. She knew what it must’ve looked like, meeting up with that cop after the way she acted. Then again, why he had called the copper “Bobby?” She knew that Meg knew about him, but, the way Dean acted, it was as though they had once been close.

As they arrived at the club, she finally took a chance. She closed her eyes and began speaking. “I swear, I didn’t go there to meet up with him.”

Dean was silent, so she continued. “Meg and I ran into him yesterday, and that’s why we left so quickly. I was scared of running into him again today. Meg told me what’d it look like, and I didn’t—”

Her eyes snapped open when she felt Dean’s calloused fingers intertwine with hers. She looked up at him, more than a little bit surprised.

He was staring at their hands, refusing to make eye contact. He must’ve noticed her look, though, since he squeezed her hand before letting go completely and getting out of the car.

She let out a sigh of relief, and followed him into the club.

* * *

It was about twenty minutes to show time, and Y/N was putting the finishing touches on her outfit for the evening. She had let her Y/H/C hair down in waves over her left shoulder and slipped into a deep forest green dress that she had fallen in love with (that definitely did _not_ remind her of anyone).

She quickly folded her clothes, trying to keep them as wrinkle-free as possible for after the show, when she felt something mixed into the pile. She frowned, searching her white shirt and brown skirt separately. She finally found the offender after rummaging around in her pockets: a small, white, rectangular card.

Emblazoned on it was the emblem for the FBI, along with the name “Robert Singer” and some contact information.

Her hands began shaking so much that she could barely read the words.

She vaguely remembered him saying that he was a federal agent, but she had been so focused on not passing out that it hadn’t clicked. This whole ordeal had been one thing when she thought him a local flatfoot, but, if the feds were involved…

A knock on her door had her shoving the business card into her cleavage before she could think. “C-Come in!”

Dean poked his head in a moment later. “You ready yet?”

She smiled, and she hoped it looked genuine. “How can a girl get ready with you pokin’ your head in like that?”

He winked. “Well, next time, I’ll just help you get ready.”

She laughed, feeling a bit more at ease. “You just gotta play your cards right, Dean,” she smirked as she breezed past him.

She didn’t look behind her as she walked down the hallway, but she figured that he was a little taken aback by her forwardness, since it took a moment for her to hear his heavy footsteps follow her.

He didn’t get a chance to snark back, however, as they met up with their bandmates. Gabe threw an arm around her shoulder, whilst Chuck rolled his eyes. Not a minute later, they were walking out to perform.

* * *

Y/N was sitting at the bar with Meg as the latter waited for her boyfriend to finish cleaning up. Conversation flowed between the three of them easily. Really, Y/N was lucky in that so many in the club were easy to get along with.

After about fifteen minutes of waiting, though, the waitress turned to the singer and said, “You’re usually one of the first ones outta here. What’re you waiting on?”

“Dean. Benny asked him for a favor before he left.”

Cas sighed heavily.

“Cas,” Meg warned.

“What?” Y/N frowned.

“I know Benny must do this, but I worry about Dean, that’s all,” the bartender explained. “He could hurt his hands, then what? I don’t understand Crowley’s thinking.”

“Is Dean okay?” the singer gripped her drink tightly.

Meg groaned, letting her head fall into her hands. “Cas, he didn’t want her finding out.”

Cas nodded in understanding. “Ah, then I’ll say no more.”

“The hell you won’t!” Y/N cried.

Meg let her head fall onto the bar, obviously annoyed, but silent.

Castiel looked to her for support, but found none. “If Dean doesn’t wish me to tell you…”

“You’re the one who brought it up, Cas.”

His pleading blue eyes found hers. “Please don’t ask, Y/N.”

“Fine,” she huffed as she pushed herself off the stool and away from the bar. “Then I’ll ask Dean.”

Castiel’s voice rang out, trying to stop her; but Meg’s soon followed, mumbling something that was definitely more than a little sarcastic.

Y/N practically stormed through the door towards the back, determined to find Dean. After searching the dressing and back rooms for a few minutes, she found herself walking down the hallway, towards Crowley’s end of the hallway and near a door she hadn’t seen before.

The door had no markings on it to tell passersby what its purpose was. Usually, when Y/N was back here, she was down at the other end of the hallway, in the dressing room or near the stage, so this was her first time seeing this specific door.

She might’ve even just walked past it, headed for the back alley or perhaps looping back to the front of the club, if not for the noises she heard.

Soft grunts and thuds could be heard coming from behind the door. She started blushing, but held her ear to the wood anyway.

Not that she was a pervert.

She was just curious.

Nothing wrong with that.

Now that she was practically one with the door, she heard voices. She could immediately pick out the condescending voice of their employer. A voice she didn’t recognize was speaking the most, however. She could make out some words, like “please” and “sorry.”

Her brow furrowed, and she strained to hear what she could.

“I’m not asking for a lot here, Mr. Morris,” said Crowley. “I’m simply asking you to hold up your end of the bargain.”

“I promise, I’m trying.”

A heavy sigh was heard, and Crowley’s voice returned, this time with more condescension. “I’m sure you are, but, well, I’m not known for my patience. Think of this visit with my minions here a little reminder of that.”

Footsteps began making their way towards her, and Y/N nearly fell over in her hurry to run away.

She was halfway down the hall when she heard the door open, and she turned to face him.

His eyebrows raised slightly at seeing her. “What are you doing back here?”

“Oh,” the singer thought quickly. “Um, I was looking for Dean. I saw him come back here, and I wanted to see if he was done with whatever he was doing.”

_Not a lie._

The club owner was still standing in the doorway slightly, which allowed Y/N the tiniest of peeks into the room. In there, she saw the large man who usually stood vigil in front of the club and who Dean considered a brother. She easily recognized Benny, and, in that moment of recognition, she knew that Dean was in there with him. Cas had said as much, and this was something that she would’ve wanted to keep hidden, too.

Crowley fully closed the door behind him at that. The sounds of fists landing and grunts of pain were immediately muffled. His dark eyes met her Y/E/C ones, and he answered, “He’s not. Obviously.”

She nodded, her eyes falling to the floor. “Oh. Okay. I’ll just, uh, go wait back out there, then.”

“How long were you listening, darling?”

Her eyes shot up. “Listening?”

He rolled his eyes. “Please, I’m not an idiot and neither are you. Drop the act.”

Y/N bit the inside of her cheek, her eyes searching him for any sign of anger. “I…not long.”

He nodded, then walked up next to her. He stopped when he was about to walk past her, and simply said, “Then you know not to cross me now, don’t you?”

She nodded feverishly.

“Because, if you do, that’ll be you, and I’ll make Dean do it. Without Benny’s help.”

Her head snapped to her left, looking up at the man. His expression held a sadistic glee, immensely pleased with his idea. “And you know that he’ll do it, don’t you, darling? Because I own both of you, no matter what sweet nothings he’s been whispering in your ear.”

Her cheeks flushed, both from his words and her anger, but she simply clenched her jaw. “Understood.”

“Good,” he began walking away. “Get home safe.”

She was stuck still in the hallway, listening to the muted sounds of the punishment from behind the door to just a little ways down the hall.

She squared her shoulders before turning on her heel and walking back out to the bar to wait for Dean.


	7. Chapter 6

Meg and Cas hadn’t moved from where Y/N had left them. They looked up when they heard her, but stayed silent. Cas looked like a kicked puppy, whilst Meg looked at Y/N with a mixture of pity and annoyance.

Y/N returned to her seat, and the three sat in silence until Dean appeared from the back about twenty minutes later.

His hands were in his pocket, and his usual grin was firmly in place. It didn’t move until he noticed the dour mood hanging over his friends. “Why the long faces?”

Cas refused to make eye contact with his friend, whilst Meg just downed her drink. Y/N sighed and stood, smiling softly at Dean. She picked up her bag with one hand and held out the other. “I’ll explain in the car.”

Dean stared at her empty hand like it was a pit of snakes.

She sighed before walking over and pulling his hand out of his pocket and pointedly ignoring the cuts along his knuckles. “Anyone would think you didn’t like me, Dean,” she teased.

He shrugged, his smile a bit more strained. “Who wouldn’t like you?”

She snuggled into his side. “You clearly don’t know me well enough, then.”

“Well, we’ll have to change that.”

She smiled genuinely at that, happy to have her regular Dean back, even if only a little bit. “C’mon, you kept me waiting long enough. Good night, you two,” she waved to their friends back at the bar. They were still a little stiff, but wished genuine good nights to them.

As they walked to Dean’s car, Y/N ran her thumbs over his knuckles without thinking. He let out a hiss of pain and a curse between his teeth.

“Sorry!” she brought his hand up closer to her.

“Uh,” he scrambled for an excuse. “I, um, I had—”

“Dean,” she interrupted. “I know, alright? I heard you all earlier.”

He stopped in his tracks at that. “You…you heard?”

“Yeah. Crowley even spoke to me after he caught me.”

Dean’s other hand immediately left his pocket and reached up to cup Y/N’s face. His stupidly green eyes searched her face, even turning it with his hand every once in a while to inspect every inch of it.

“He didn’t hurt me, Dean, don’t worry. Just threats.”

“He’ll back them up, Y/N.”

“I know.”

There was a beat of silence before Dean spoke again. “I didn’t want you to find out.”

She shrugged. “Don’t worry about it.”

He frowned. “Don’t worry about it?”

She looked up at Dean, making eye contact for the first time. “I know you’re a good man, Dean Winchester, no matter what Crowley makes you do. Now, let me take you home and get these hands of yours cleaned up.”

He seemed awestruck, like a meteor shower had interrupted his regular old stargazing.

She squirmed slightly, but didn’t get a chance to say anything.

Before she could really think, his lips were brushing up against hers. Those amazingly plush lips she had been fantasizing about since the moment she met him were pressed ever so gently against hers.

He pulled away a moment later and, without thinking, Y/N’s hands were on his neck and pulling him back against her. Like hell was she going to pass on this opportunity.

The hand she hadn’t been holding was gripping her hip like a lifeline, shoving the two of them as close together as possible. The hand that Y/N had dropped was clutching the hair at the nape of her neck, angling her head for the best possible position.

Fire burned under her skin and she could hardly breathe. She felt herself being pressed up against ice cold metal of what was undoubtedly Dean’s car, but it did nothing to cool her down.

She finally had to pull away when she felt she might pass out. Dean followed her for a split second as they separated, breathing as heavily as her.

His hand left the nape of her neck to cup her cheek and he let his forehead fall lightly against hers. Silence hung in the air for what was probably the longest moment of her life before she finally breathed out a “Wow.”

He chuckled at that. “Been wantin’ to do that since I saw you.”

She huffed out a laugh. “Same here, handsome.”

His eyes finally opened and locked with hers. “I…I want you to be my girl.”

She bit her bottom lip, trying to reign in her excitement. “I didn’t hear a question there.”

He groaned playfully, the hand on her hip pulling her even closer, if possible. “Please?”

“Well, how could I resist?”

* * *

 

She wasn’t entirely sure how she got here.

Dean had managed to convince her to join him at his apartment to fix up his hands, and even offered to let her stay the night.

She’d agreed, mostly because he had his lips against her neck and, really, how was she supposed to focus on anything else?

So, now, she was standing in the hallway outside of his apartment, and he was fumbling with his keys with his left hand, as his right hand hadn’t managed to separate itself from hers just yet.

When they finally entered, Y/N smiled softly. It was a small place, to be sure. It was barely filled, with a tiny kitchen off to the left, a living room just part that, and what looked to be the bedroom and bathroom off to the left. In the living room sat a small loveseat in front of a TV set. A bookshelf sat off to the right, its shelves filled with pictures and a few token books.

What really made it seem like Dean’s place, however, was the phonograph in the corner, with a shelf stuffed with records.

He led her over to the loveseat, offering her a drink. She asked only for water, her throat already dry enough.

He disappeared into his bedroom for a moment before returning with a basic first aid kid, then went off to the kitchen.

Thankfully, there was a low coffee table made of a dark wood sitting in front of the loveseat, so Y/N pulled out everything she needed.

Dean announced his presence to her by holding out the small glass of water, which she took gratefully.

He sat down beside her with his own glass of appeared to be whiskey. He laid back against side of the couch, and took a large gulp of his drink.

“You know, it won’t hurt _that_ bad, Dean,” she teased, putting hydrogen peroxide onto a cotton bud.

He chuckled. “With how rough you were bein’ earlier, I don’t wanna take any chances.”

She turned bright red at that. She tried to stutter out a comeback, but instead, mumbled out a “C’mere” and took his free hand in hers.

He only let out a light hiss when the cotton swab brushed gently over his knuckles. Y/N carefully dabbed at all his knuckles before pulling out some bandages. She wrapped his hand as tightly as she could without hurting him.

When she finished that hand, it fell on the back of the couch, almost around her shoulders. He pushed himself impossibly closer, placing his now-finished drink onto the coffee table before holding out his right hand.

She didn’t say anything about his proximity, instead focusing entirely on cleaning up his dominant hand. Sure, she could practically feel his eyes boring into her, but she had to make sure Dean was okay first.

His left arm fell slowly off the couch, his fingers trailing feather-light down her arm to her waist. As Y/N finished up, his hand slipped around to the small of her back.

“Dean…” the word was supposed to be a warning, but it came out more as a moan.

The bastard smirked before pulling her close and slanting his lips over hers. Y/N dropped the last of the bandages she was holding and to grab hold of his shirt. The idea of separating from Dean was suddenly the most horrifying thing she could’ve thought of.

Before this evening, Y/N had never even had the occasion to kiss a man, let alone pull at him so wantonly. It seemed as if he was consuming her, bit by bit, and she wanted nothing more than to let him.

She only pulled away to trail her lips along the side of his jaw and down his neck, as he had done earlier. She was nothing if not a quick study.

“Should we take this into the bedroom?”

That stopped her cold.

She nearly leapt out of Dean’s arms, putting as much distance as possible between the two of them.

His face was filled with several emotions, the chief ones being confusion and concern (followed closely by lust). “Y/N?”

“Um,” she began, already searching for the words to describe what was wrong. Lord knows _he_ hadn’t done anything wrong.

“I’m sorry, sweetheart,” he began almost immediately. “I didn’t mean to rush you or anything. I just—”

“God, Dean,” she shook her head. “No, it’s just…you have been amazing. I just…I’ve never…”

“Oh,” his eyebrows raised to match the higher octave his voice had taken on. “ _Oh_ , I…”

“I mean, I’d never even _kissed_ a boy before, and—”

“Whoa, you’re tellin’ me that you ain’t ever even kissed somebody?” he smiled. “Shit, doll, you were sure actin’ like it.”

She flushed at that, but laughed anyway. “Well, I had an excellent partner.”

Dean stood, his smirk losing a bit of its original mirth. “I’m sorry, doll. We don’t have to do anything tonight, okay?”

She relaxed at that and even reached for his hand. “Thank you. I’m sorry, I should’ve said something earlier.”

He took her hand in his. “You already agreed to be mine, that’s enough. For now.” he added with a wink.

She chuckled, wrapping her arms around him and nuzzling her head into his chest. “Thank you.”

His hands wrapped around her waist, fingers linking together at the small of her back. She felt a feather light kiss placed at the top of her head.

Finally, Y/N pulled away and grinned. “C’mon, we need some sleep if we wanna deal with all the comments about this,” the motioned between them. “Tomorrow.”

Dean laughed. “Please, I’ve been dealin’ with Gabe’s comments since you started.”

She pushed herself fully out of Dean’s arms, moving to pack up all the first aid items she’d left spread out haphazardly all over his coffee table. “Sounds about right. Sorry about that.”

He shrugged. “Come on, clean that up tomorrow.”

She didn’t even pretend to fight him on that. “Do you have a pillow and a blanket I can borrow?”

“Yeah, on the bed.”

She flushed a bit at that. “Dean…”

“What? I didn’t think we _wouldn’t_ be sharing the bed tonight!” he cried in self-defense.

She frowned, feel more than a little guilty. “…good point.”

He threw an arm around her shoulder, leading her to the bedroom. “Don’t worry about it. I’ll stay out on the couch, and you’ll get the bed.”

She shook her head. “No, I can take the couch, Dean. You’re much too tall for it.”

He shrugged, acting incredibly nonchalant. “I’ll be fine. Won’t be the first time.”

She chewed on the inside of her cheek. “You’re sure?”

He opened the door to the bedroom, revealing a rather large bed that barely fit in the small apartment. He pressed a quick kiss to her lips, pulling away before either of them got caught up in it. He walked over to the dresser shoved into the corner. He pulled out not only his pajamas, but one of his shirts for her to sleep in.

She took the shirt and repaid him with a soft smooch, one of the blankets from the bed, and a pillow before he left, closing the door behind him.

She waited a moment before silently fangirling right the fuck out.


	8. Chapter 7

She should’ve been woken up by the light streaming in through the window right into her face, but she had just rolled over and gone back to sleep.

Maybe the sound of Dean fumbling around the kitchen, clanking pans together should’ve woken her up, but she just moved the pillow from under her head to over it.

Actually, what woke her up was relatively unobtrusive.

His phone rang.

The shrill tone broke through the pillow like a needle through cloth, straight into her ear. She sat up, groaning. She took a few moments to mentally prepare for the day before throwing her feet onto the floor.

Then she heard that deep, gravelly voice that had haunted her dreams the night before. She bit her bottom lip, excited at just the very idea of seeing him first in the morning, of spending every moment of that day with him.

“Look, Bobby, I can’t talk right now.”

Her heart nearly stopped.

A moment of silence passed before he spoke again. “No, of course I…Bobby, you’re family, you know that. But you know what he’ll do to Sammy if he finds out we saw each other.”

She didn’t know any “Sammy.” Thinking on it, Y/N didn’t know a lot about Dean’s past. Everyone in the club liked to keep mum on it, no one willing to bring up the reason they were now indentured servants.

There was another moment of silence before Dean’s voice, albeit softer than before, came through again. “Yeah, her too…m-maybe…she’s important, alright? Can we leave it at that?”

She grinned, practically able to hear his blush through the thin walls.

“Look…” he began. “I knew what I was doing, alright? And I’d do it again, alright? Sammy’s fine. He’s marryin’ his girl soon, ain’t he? He’s happy. That’s all I need.”

There was another moment of silence before Dean grumbled out, “I get it, Bobby, I do, but…don’t ask me to do that, please. I can’t take the chance that Sammy could get hurt… _no,_ don’t you go after Y/N either. I’m not losin’ anyone else.”

He practically slammed the phone back onto the receiver, and the deep sigh he gave resonated within her. She was on her feet and through the doorway before she could think.

The moment the door opened, she was hit with the tantalizing smell of coffee and the frankly amazing sight of Dean Winchester in his undershirt and pants, suspenders hanging from his hips, standing at the kitchen counter with his back turned to her.

His head snapped in her direction when he heard the door open. A big smile spread across his face and he greeted her with “Damn, baby. A fella could get used to this.”

This was the exact moment that Y/N remembered that all she was wearing was his shirt.

A part of her wanted to run back into the bedroom, change into her clothes from yesterday, and put this moment behind her.

The part that won, however, decided that she would own this. She padded into the kitchen and sidled up next to him, wrapping her arms around his waist.

She grinned up at him. “Well, _I_ could get used to _this_ , so it’s only fair.”

He laughed. “That’s my girl.”

One of her hands reached up to grab the back of his neck. She pulled him down as she climbed onto her tip toes to press her lips to his. “All yours.”

* * *

 

They made themselves some breakfast and, at some point, Y/N had ended up on the counter with her legs wrapped around Dean’s waist, the two of them connected at the lips.

Then, he had a _very_ long shower before they went to her hotel to get her a change of clothes. She had taken all of ten minutes, the first one or two being spent on telling Dean that, yes, she could get dressed without his help.

Then, they were at the club. They hadn’t even entered before Benny clapped Dean on the back. “Took you two long enough.”

Dean just laughed, but Y/N had to ask, “What gave us away?”

Benny stared at her like she’d grown a second head. “Really? You two come in with stars in your eyes and holding hands. I ain’t an idiot.”

It was then that Y/N noticed that they were in fact holding hands, their fingers intertwined. She looked up, narrowing her eyes at the pianist. “Smooth moves there, Winchester.”

He’d just pressed a kiss to her temple, before throwing a “see you later!” at his friend and moving them inside.

“Oh, and tell Gabe he owes me five dollars!” Benny shouted behind them.

Dean laughed, pulling his hand from Y/N’s and throwing it around her shoulders. She settled herself into his side, sliding her arm around his waist to rest her hand on his opposite hip.

The moment they walked into the bar, Castiel smiled warmly at them, and Meg even smiled as she rolled her eyes. Chuck ordered a round of drinks for everyone (making sure to tell Cas to put them on Gabe’s tab), and they had a few minutes of frivolity before getting back to work.

Gabe came in grumbling. He was happy for the new couple, of course, but he was sure it’d take another month for Dean to make a move. “You owe me, Winchester!”

Dean had laughed him off, but the drummer seemed quite serious.

As they sat there, laughing it up with everyone else, Y/N’s fingers intertwined with Dean’s. When he squeezed her hand back, she felt the blood rise in her cheeks and a smile nearly split her face in half.

* * *

 

“Well damn, that was the best show we’ve ever had!” Gabe was breathless. He threw an arm around Y/N’s shoulders and pulled her close. “Doll, you were amazing!”

She laughed at that. “I’d be nothing without my boys!”

Gabe squeezed her shoulders. “Please, we’d be nothing without our canary.”

She felt a tug on her other hand and she was suddenly yanked from Gabe’s hold against another’s chest. Looking up, she was met with the jade green eyes of her Dean. His arms immediately wrapped around her shoulder, holding her in place.

The drummer laughed at that. “Oh, please, Dean-o. You won’t be able to tell I’ve stolen her from you ‘till she’s mine.”

Chuck and Y/N snickered at that, but she felt Dean’s arms tighten around her. She didn’t need to look up to see the tightened expression on his face. However, she still put her left hand on the side of his face, standing on her tip toes and pulling him down so she could place a kiss on his free cheek. He relaxed immediately under her lips, and she let herself fall back against his chest in peace.

Gabe made several unsavory comments, elbowing Chuck and obviously pleased with himself. Dean just grumbled quietly and squeezed her closer.

Meg appeared backstage at that point, walking through the door. Somehow, even after working the past few hours, she looked just as beautiful as she had when starting her shift earlier that evening. “Hey Dean-o, Benny’s askin’ for ya.”

Y/N gripped Dean’s arm tightly, which caused Meg’s eyes to fall to the position the singer and pianist were in. “Sorry, Y/N.”

Dean stiffened a bit, and the formerly jovial tone in the room turned cold. Y/N felt his lips press against the top of her head. She closed her eyes, relishing in the feeling as his arms dropped from around her. Goosebumps rose over her flesh where his heat had been pressed up against her, and she fought a shiver from running down her spine.

Before Dean could say anything, Y/N spun around, a big smile on her face as she put her hands on his chest. “Chuck promised to tell me ‘bout his latest story, so don’t wait up.” She leaned up and pressed a soft kiss to his lips, hoping that she could convey, with just that, that everything was okay.

He gripped her upper arms just a little too tight as they kissed. She pulled away a moment later, but Dean didn’t seem quite ready to go.

She gripped his shirt in her hands and looked him right in the eyes. “It’s okay,” she whispered. “Just gives me an excuse to spend the night at your place, don’t it?” she teased.

He actually cracked a smile at that. “Lookin’ forward to it.” He finally turned and walked away.

There was a moment of silence before Y/N felt a hand on her shoulder. She turned to see Chuck smiling at her. “C’mon, I can’t make you a liar.”

She smiled as she thanked him.

“I thought you weren’t working on anything right now, Chuck,” Gabe thought aloud.

Chuck shrugged. “I’ll think of something.”

Meg leaned against the wall. “Maybe you can tell her the story of how you got to be such a sad sack.”

Chuck answered with a fake laugh and a “Don’t you have anything better to do?”

Meg threw her hands up in self-defense before walking back into the main room with a self-satisfied smirk.

“Alright,” Chuck began, putting a finger to his chin and looking up, pretending to be thinking quite hard. “Now, I need to come up with a story for you.”

Y/N and Gabe laughed. “Oh, can it be a thrilling tale?” she asked.

“Naturally!”

Gabe spoke next. “One with action!”

“And drama!” she joined in.

“And romance, of course!” Gabe teased, needling the singer.

Y/N rolled her eyes at that, pushing him playfully.

She could practically see the idea hit Chuck, and he took hold of Y/N’s hand to begin dragging her towards the back room. “I’ve got it!”

“Careful there, Chuckie—looks like you’re trying to steal Dean’s girl.”

“Well, I certainly like to be romanced more than this.”

Chuck ignored them, pushing open the door to the dressing room. Y/N sat in her usual chair by the mirrors, whilst Gabe leaned against the wall next to the door and Chuck paced the room.

The bassist grinned, more excited than Y/N had seen him before. He looked like he was getting ready for a performance and was walking off the nervous energy. “Alright, you ready?”

“I better be. You look ‘bout ready to explode!”

He grinned, his eyes twinkling. “Alright, well, this is a story about two brothers…”


	9. Chapter 8

“Once upon a time, in a kingdom far away, there was a family. They were just like every other: a loving mother, a doting father, and two young boys.

“Then, one night, when the boys were just babes, their mother was taken from them, lost in a dragon’s fire that destroyed the only home they’d ever known. This broke a strong man, and their father eventually lost everything he had to getting revenge…everything except his sons.”

“Chuck…” Gabriel warned, his voice lower than Y/N had ever heard.

“The elder son became the parent to the younger. He scoured the land for work, for safety, for anything to protect his brother. He fought, he stole—he did whatever he needed and never complained.

“The boys grew up, big and strong. Whenever their father was around, he trained them, made them into the best soldiers he could in the fight against the dragon. The younger son grew to hate his father, grew to hate his life, and so, one day, he left his family to find his own way in the world.

“Eventually, the father’s quest for revenge killed him, and the boys were truly alone. The older son went to his brother and threw himself into protecting him. Nothing else mattered.

“Then, the younger brother was cursed. He was dying, and there was nothing that could be done. Nothing but the unthinkable.

“So, the older brother went to a powerful and evil wizard. In exchange for saving the youngest’s life, the older sold himself to the wizard, to work in servitude for him forever.

“The younger brother was cured and the curse had left no trace. He was free to live his life as he wished, never to know what his brother had done to save him.

“The older son watched from afar as his younger lived his life: he met a beautiful princess and they decided to wed.”

“Chuck,” Y/N began, unsure of what she was going to say next. She felt like she was violating Dean’s privacy just listening to this, but she wasn’t able to stop.

“The older son made friends with the others in servitude, and he was as content as he could be. But then came a siren, a beautiful creature that captivated the him.”

“I think I know this part, Chuck,” Y/N interrupted, wringing her hands together.

“Plus, don’t sirens lead men to their deaths? That’s not a very nice thing to say about Y/N,” Gabe tried to ease the tension in the room.

Chuck frowned. “Okay, I need to work on it, obviously.”

Y/N stood. “Does Dean know that you’re doing this?”

The bassist shook his head.

“I can’t imagine he’ll be all that happy when he finds out,” Gabe added, sighing.

Before Chuck could retort, however, a knock came at the dressing room door. Castiel stuck his head in the door with an apologetic look on his face. “I’m sorry, but would you mind joining me, Y/N?”

The singer looked between her bandmates before nodding. “‘Course, Cas.” Before she followed the bartender out into the hall, she turned to her bassist and smiled softly. “Thanks, Chuck.”

He smiled half-heartedly back at her. “Happy to help, Y/N.”

* * *

Y/N had ended up helping Castiel with some inventorying. She quickly figured out that he didn’t need any help, and she assumed that Dean had asked him to keep her company whilst he was busy.

She couldn’t be happier to know that Dean had such good friends.

Chuck had put a paper thin pretense over his story, but she wasn’t an idiot. Sure, some of the details might be a little fuzzy, but she knew the main parts: his parents were dead and he had ended up with Crowley to save his younger brother’s life.

She wasn’t sure how long she’d spent with Cas, though Meg came by a few times to check in, make sure everyone was okay and to show some measure of quiet affection with Castiel.

Y/N watched them with a soft smile. It was always subtle. A hand on the arm, standing just a tiny bit too close to each other, eye contact holding just a tiny bit too long. There was a quiet content intimacy between them, unspoken but comfortable.

Y/N found herself hoping that she and Dean would be like that one day.

Finally, the man himself came out. He had a small cut on his bottom lip and looked a little more rundown, but was otherwise fine. Y/N rushed over to check on him, immediately placing her hands on either side of his face.

He smiled down at her. “Don’t worry, doll, I’m fine.”

She sighed dramatically. “Good. I’m only with you for your looks.”

He laughed at that, a bit of weight leaving his shoulders. “C’mon, let’s go home, sweetheart.”

Y/N stopped him, frowning. “Is Benny okay?”

Dean nodded. “Yeah, he’s fine. Plus, you’re _my_ nurse, and I ain’t sharin’.”

She twined her arm with Dean’s and rolled her eyes. “Glad to hear you care so much about your friends.”

He chuckled. “C’mon, let me be selfish with you, doll.”

Pink dusted her cheeks at that and she shrugged, mumbling out a “Guess I can let ya off the hook for that this one time.”

They waved goodbye to everyone, got in the car, and were at Dean’s apartment before she could blink. She took the same seat she had the night before, and he disappeared to get the first aid kit. When he returned, Y/N got right to work, disposing of the new bandages and rewrapping his hands.

“So, what story did Chuck tell you?” Dean asked after a few moments of silence. “Or did Cas save you in time?”

“N-No, he didn’t,” She gulped and refused to look up at him.

“Ah, so you had to listen to one of his tall tales. Alright, which one was it?”

“Yours.”

“Mine?” she could practically hear the frown in his voice, and she didn’t need to look at him to see the furrow between his eyebrows where they drew together.

She nodded. “Not everything, I don’t think, but he told me about your mom, your dad, your brother…”

The cozy, quiet, comfortable atmosphere that had been in the room turned cold.

“I’m gonna kill him. He shouldn’t’ve told you that,” he practically growled.

There was a moment of unbearable silence. She couldn’t bear to look up and see the disappointed look in his eyes and know that she put it there. She would’ve felt the same, so she couldn’t blame him.

Without thinking, she began speaking, “You know, I grew up in an orphanage.”

He started at that, which she scolded him for. “Don’t move, Dean!”

“Wasn’t expectin’ that, is all.”

“Well, I did. Then, y’know, things got real bad. Couldn’t afford to keep all of us. So, I left when I was fourteen. Didn’t like anyone there anyway.”

“Y/N…you don’t have to tell me anything.”

She finally locked her Y/E/C eyes with his emerald ones. He looked confused mostly, but what she also saw was concern. He cared about whether or not she was comfortable. Her heart swelled at that thought, and she gave him a lopsided smile. “I trust you, Dean.”

His eyes widened at that, and he seemed to be struck speechless.

So, she continued. “After leavin’, I was on the street. Lived mostly at those soup kitchens, y’know? Slept under bridges and with old ratty coats I found in the trash. Finally got a job ‘bout a year ago. Workin’ at a bank, like a real, respectable lady.

“And people kept comin’ in with all their money, flashin’ it everywhere. Some of them were savin’ pennies, but others? They had so much and they were so cruel. So I…” she gave a humorless laugh. “So I decided that somea us deserved it more. That _I_ deserved it more.”

“Please tell me you didn’t.”

“Wish I could.”

His hand reached up to cup her face, his thumb stroking alone her cheekbone. “Oh, sweetheart…”

She shrugged, focusing again on his hand. “I got caught pretty quick. Then I went to the big house, stayed because I couldn’t afford to get out. I couldn’t sleep in there. Everyone was so loud, and there was always someone shoutin’ ‘bout something and…and the only way I could get to sleep was to sing myself a lullaby. Calmed me down enough to rest. That’s where Crowley found me. Said he wanted to free the caged bird. All I had to do was sing in his club, and I’d be out. From where I was sittin’, seemed like the better deal.”

Dean sighed and pressed his lips to the crown of her head. “Thanks, doll,” he whispered into her hair.

She looked up at him and smiled softly. “Fair’s fair,” she leaned up and pressed a soft kiss to his lips. “Felt like you should know.”

“Makes sense why you were so afraid of Bobby.” He mumbled absentmindedly.

Her eyes widened and she froze a bit.

He noticed, of course. “Oh, shit, baby, I—”

She shook her head. “I think that’s enough for one night, don’t you?”

He let out a soft sigh of relief. “You’re amazin’.”

“I know.”

He laughed as he leaned in for another kiss.


	10. Chapter 9

“Shit.”

It was shortly after opening, and Y/N was leaning over the bar with Meg, both of them holding bottles of various spirits as Castiel cleaned up a spill.

The singer looked up, following the waitress’ eye line to see what has caused the spontaneous curse.

Agent Singer had just walked through the doors of Crowley’s along with a black man of a similar age and dress. Benny was standing in front of them, tense as she’d ever seen the man. Though they couldn’t hear the discussion from the bar, they could feel the pressure of the conversation from where they stood.

Meg’s knuckles had turned white as she gripped the bottle of tequila almost to the point of breaking it. Cas’ hand came from seemingly nowhere to cover her hand in comfort, but it did little. “What the hell are they doing here?”

Y/N couldn’t answer.

Finally, Benny seemed to lose the argument, and stepped aside. Y/N could almost hear the threat he must’ve given to the two men.

They walked inside the almost-empty nightclub, making their way immediately to the bar. The girls tensed, but Castiel stood and, without a trace of fear, simply said, “You’ll have to excuse me gentlemen. I spilled some water, and you will have to wait until I’m finished cleaning it up before I can serve you anything.”

Agent Singer waved him off with a “take yer time,” but the other man simply grumbled something about Blue Label scotch.

Meg and Y/N stayed stiff as boards as Castiel cleaned a little faster. He took bottles from Meg first, so she could get away sooner. Meg gave him a grateful smile before running away like the devil was on her heels.

When he was ready, Y/N shoved the bottle of vodka into Castiel’s arms before mumbling a goodbye to him. As she circled around the bar, heading for backstage, when she felt a hand on her arm.

Benny was at her side in practically an instant, before Y/N even had the chance to realize that it was Agent Singer who had grabbed her, stopping her in her tracks.

“What’d I say ‘bout causin’ trouble?” Benny nearly growled. “Hands. Off.”

Bobby looked between Y/N and Benny before letting go of her upper arm. “Sorry, didn’t mean to start anything. Just wanted to talk to her.”

“Well, she’s gotta go get ready for the show,” Benny moved in between the cop and the singer, and she’d never loved the man more than she did in that moment.

“It’ll only take a minute,” Agent Singer argued, looking a little frustrated.

Benny looked back at her, silently asking her what she wanted to do.

With a minute shake of her head, he had whirled back around on the federal agent and smiled coldly. “Well, next time, come in earlier. Now, you can either sit there and let her go get ready, or you and your friend can leave. Your choice.” Benny had an uncanny knack for sounding polite and gentlemanly whilst also making someone fear for their immortal soul.

The copper’s jaw clenched, but, before he could say anything, his friend had placed a hand on his other arm. “Bobby, let the girl get ready. Lord knows I need a drink first.”

Agent Singer grumbled, but nodded. “Fine, sorry, miss.”

Y/N gripped the back of Benny’s shirt, and he took the hint. He escorted her backstage, calling for Dean the moment the door was open.

The pianist came out a moment later, looking a bit confused. “Benny, what’re you doin’ back here?” then his hunter green eyes fell on Y/N. “Baby? What’s wrong?” he rushed over to her, placing one hand on each of her cheeks.

Y/N wrapped her arms around Dean’s middle, drawing in a shuddery breath as Benny answered. “Bobby and Rufus are here.”

Dean entangled the fingers of his right hand in Y/N’s hair, holding her tightly against his chest. His left hand wrapped around her shoulders as he nodded at Benny. “Alright, I’ll go talk to ‘em.”

“You know how that’ll look, brother.”

“He can’t blame me for talkin’ to family, Benny.”

Y/N tensed at that. Dean and Agent Singer were related?!

“He can blame you for anything and you know it.”

Y/N pulled back. “Please, just…can’t we just ignore him?”

Dean leaned down to press a soft kiss to her forehead. He didn’t say anything, just gave her an apologetic smile before letting her go and walking out front, leaving her with Benny.

She turned to the bouncer and begged him to go back Dean up.

Benny laughed, his blue eyes crinkling. “Dean can sure as hell handle himself. Cas is there, too. He’ll be fine.” He wrapped an arm around her, hugging her close. “Don’t you worry ‘bout Dean. He’ll be fine.”

She almost believed him.

* * *

 

Their performance didn’t suffer that night, even though all Y/N could feel was the agents’ eyes resting on her.

Dean hadn’t come back from his talk with the agents until just a few minutes before they went onstage. She hadn’t had a chance to talk to Dean all evening yet, and questions were burning within her.

However, a part of her didn’t want to bother him. It had only been a month since that night where his entire past had been revealed to her, and perhaps he wasn’t ready to share more just yet.

After all, they were just newly together. They would drive to and from Crowley’s and, every night, Dean would try to find an excuse for her to spend the night. He hadn’t had to help Benny with any extra work since that last time, so he’d come up with anything to get her to stay: Her motel looked unsafe. He couldn’t find his way to her motel, so she might as well come home with him. He saw a spider in his apartment and needed her to protect him.

The excuses got more and more outlandish every night, and she was convinced that he was more trying to make her laugh than convince her to stay with him.

However, every night, she would shake her head and smile, claiming that she shouldn’t, not until they could share a bed. He reminded her that he didn’t mind the couch, but she would stop his argument with a kiss, and then all words would stop for a while.

Y/N had to shake those thoughts from her head. All those thoughts just raised her body temperature and made it harder for her to formulate coherent thoughts.

At the end of their first set, Y/N nearly pulled Dean off to a dark corner for them to talk. Gabe usually made jokes about the two of them needing some space, but, tonight, their usual jovial tone was on vacation.

When they got to the dressing room, Y/N whirled around on Dean. However, before the words could leave her, his lips crashed against hers. He pushed her up against the door they had just walked through, caging her in.

On instinct, her hands were immediately fisting themselves in his shirt, pulling him closer. She felt his hands encircle her, and, within no time at all, every one of her senses was consumed by Dean.

Then, her eyes snapped open, and she shoved Dean away. He pulled back, still holding to her tightly, a pout on his stupidly beautiful lips.

She frowned. “You bastard, you’re not getting away that easy.”

He laughed at that, letting his forehead fall against hers. “Worth a shot.”

Her fingers intertwined behind his neck. “I just wanna make sure you’re okay.”

He pulled away just a bit so he could look in her eyes. “You don’t have questions ‘bout Bobby?”

“Oh no, I’m just _dyin_ ’ to know.” He nodded, seeming unsurprised. “But, with how I found out ‘bout your past, I wanna have you tell me everything else when you’re ready.”

His fingers traced along her cheekbone. “How’d I get so lucky?”

She shrugged. “I have low standards.”

“Thank God,” he grinned as he leaned in, kissing her again. Where before, his kisses had meant to be passionate and distract her, this one was about simply being with her, the comfort and intimacy they shared in that moment.

There was a knock at the door, and Chuck’s voice carried through, letting them know that it was nearly time to go back on stage.

Y/N disentangled herself from Dean to run to the mirror and reapply her lipstick before taking his hand and heading back onstage.

* * *

 

Finally, the night was over, and they were clearing up for the evening, preparing for another day.

The agents were still there, so Y/N made sure to stay by Dean’s side as they got ready to leave.

Before they could, however, Crowley came out from his office. He walked up to the agents, giving his usual smile that was supposed to be welcoming, but usually just made people uncomfortable. Then again, it was entirely possible that was his intention. “Well, gentlemen, I hope you enjoyed yourselves tonight!”

Agent Singer turned to face him, but his expression didn’t move from its usual gruff look. “The band was great.”

The other man—she assumed that was Rufus—held up his glass. “You definitely got the good shit here, too.”

“Only the best, of course,” Crowley drawled. “And not to berate my own establishment, but I do wonder what brings two upstanding officers such as yourselves here this evening?”

Rufus raised his glass once more. “You got Johnnie Walker Blue. That’s all I need.”

“There are other bars, other nightclubs with that kind of scotch, Agent Turner.”

“Other bars don’t have a band like yours,” Bobby said pointedly.

Y/N grabbed Dean’s arm, her knuckles white. The pianist maneuvered himself in front of the singer as quickly and subtly as he could.

Crowley’s hazel eyes fell on the couple, and he nodded. “Ah, yes. Family and all that, of course.” There was a tense silence before he continued. “Well, as lovely as it’s been to have you here, the bar is now closed, so I’m going to have to ask you to leave for now.”

The agents stood. Rufus was halfway into his coat and out the door, but Bobby looked reticent, his eyes trained on Dean. Dean refused to make eye contact, instead focusing on Y/N’s hand wrapped around his arm.

Y/N, however, met the older man’s gaze. She gulped, but refused to break. She was shaking and she knew that Dean could feel it.

Agent Singer’s gaze softened after a moment, and, suddenly, he was breaking her heart rather than terrifying her. None of the cops she’d met in her short time with the Chicago P.D. had shown any sort of humanity, seeming to her like cold, heartless robots.

Maybe it was the fact that he was related to Dean somehow, and the two obviously held great affection for each other. Maybe it was the fact that he looked so tired, yet still so determined. However, in that moment, Y/N’s fear was lessened immensely.

Then the moment was over.

“Well, we’ll have to come back another time then,” Agent Singer said as he slowly stood up, shrugging his coat on.

“You’re more than welcome to any time!” Crowley grinned a grin that never reached his eyes.

The tension in the room didn’t even dissipate once they left. Everyone stood stock still until they heard Benny close and lock the front door behind the agents.

There was a terrible moment of silence before Crowley turned to them. Rage burned behind his eyes, and she had never seen someone’s face so red in her entire life. Her hands drifted down his arm to Dean’s hand, intertwining her fingers with his hand. He gripped it so tightly that she felt the tips of her fingers start to tingle from lack of blood.

Crowley took a deep breath through the nose before speaking in a terrifyingly even tone. “Who brought them here?”

Y/N wasn’t sure where to keep her eyes. She feared that looking at Dean or Meg would bring Crowley’s wrath down upon them. Then again, if she looked at the floor, she might look guilty. So, she focused on Crowley’s tie, afraid to look him directly in the eyes.

The following silence was louder than anything they’d played that night.

Crowley straightened his back, running his hands over his suit jacket, trying to smooth it out. “Fine. I know who it was. Dean,” he glared at the pianist. “You have an appointment with Benny. _Now._ ”

Y/N opened her mouth to say something, but Dean seemed to sense that. “He’s family, Crowley.”

“Family who has dedicated _years_ to putting me in jail. Family you sat and chatted with about God knows what before the show. Forgive me for being skeptical.” he growled back.

Y/N watched Dean’s jaw clench, and, out of the corner of her eyes, she saw Benny slump his shoulders almost imperceptibly.

“Please,” she began. “Dean didn’t invite him, Mr. Crowley.”

“Oh? Why do you say that, dearie? Did you?”

“N-No, of course not! But, but Dean wouldn’t put Sammy at risk like that!”

“Dean does a lot of stupid things. Like fuck the new chippy.”

Dean took a step forward, but Y/N’s ironclad grip on his hand kept him grounded enough before he did something stupid.

However, Crowley saw the step, and, in his mind, it was enough. “Benny! Here, now!”

Benny walked up to the rest of the group slowly, obviously trying to procrastinate. “Sorry, brother,” he mumbled, just loud enough for them to hear. They all knew what was coming.

Dean gave a small nod to his friend—his silent way of forgiving the bouncer for what was about to happen—before turning to his girl and smiling softly.

She gave his hand a squeeze, desperate for some way to save both boys from this. Dean had to pry his hand from her grip before walking towards Benny, his head held high.

Benny turned to Crowley, who gave answered with a wave of his hand.

Before anyone could blink, Benny’s fist connected squarely with Dean’s jaw.

Crowley shouted, “Benny! Not the face!”

Benny swallowed thickly, before turning back to his best friend and slamming his fist into Dean’s stomach. The sound of all the breath in Dean’s body leaving him was one of the worst things Y/N had ever heard.

She wanted nothing more than to throw herself into the fight, stop the senseless beating, especially when Dean fell to his knees. She was a coward, though, and stayed stock still, tears flowing freely down her face.

Benny caught her eye at one point, and it just reminded her that Benny was also the victim in this. She smiled sadly, hoping to silently convey that this wasn’t his fault.

“Come on, Benny,” Crowley rolled his eyes. “I can tell when you’re holding back. I’ve not heard a bone break yet.”

Benny’s shoulder slumped a little more, and he looked to his friend. Dean nodded, his jaw clenching.

Benny reared back, and Y/N hid her face in her hands, refusing to look anymore. The sounds of Dean’s breath and blood leaving him still rung in her ears, and it was a thousand times worse to imagine what he was going through than to see it. After a moment, she let her hands fall, steeling herself to watch the beat down in front of her.

Finally, Crowley’s voice rang out, “You can stop now, Benny. Still need him to play tomorrow night.”

Benny was breathing heavily, his face red from exertion. He was staring at the ground like it held all of life’s secrets. Dean was on the ground, his back to Y/N and his face covered by his hands.

It was silent, save for their heavy breathing, until Crowley spoke again. “Well, I found this to be quite enlightening, didn’t you? Now, I won’t see anyone speaking to either of our government’s finest again, will  I?”

The silence continued.

“Excellent. Oh, and don’t let his blood stain the carpet,” he added before heading into the back.


	11. Chapter 10

There was a long moment as they all listened to Crowley’s footsteps fade. Benny was the first one to break. “Cas, get some ice.”

Castiel nodded, and Meg joined him, saying that Benny would need some ice himself.

Y/N practically ran the two or three feet of distance between her and her boyfriend, both hands on his cheeks within seconds. “How ya feeling, Dean?”

He took a moment before wincing out a grin. “Better now, doll.”

Benny and Y/N helped Dean to his feet, though one was able to help far more than the other. They led him to a booth, and she beside him. He took the opportunity to rest his head on her shoulder.

Benny went off, mumbling something about the carpet, and leaving the two alone. She took one of his hands in hers and used her other hand to run her fingers through his short hair.

“Does…” he began, making her look down at him. “Does this mean that you’re staying at my place tonight?”

She laughed, trying to at least not move her shoulders too much. “Dean…”

He looked up at her, his green eyes wide and begging. She leaned down just a smidge to press a kiss to his brow, right between his eyes. “Of course I will. Not that you’re sleeping on the couch.”

“You’re right,” he smiled. “I need my nurse to stay right by my side all night.”

She rolled her eyes, but didn’t argue, as she saw the bartender walking over, holding a small dish towel wrapped around a handful of ice. She thanks Cas with a soft smile as she took the makeshift ice pack from him. She turned to Dean and asked quietly, “What hurts the most?”

“My lips.” he grinned. “Wanna kiss it better?”

Y/N playfully glared at the pianist as Castiel spoke, “I’m glad to see your sense of humor was not hurt.”

“Benny’ll have to learn to hit harder in order to get that,” Dean shrugged, trying to hide the wince it caused.

She heard Benny chuckle from his spot on the floor in the middle of the club. “Didn’t wanna hurt your ego in front-a your girl.”

“Please,” Dean scoffed, taking the ice pack from Y/N and placing it against his left ribs.

“Dean, go home—we’ll take care of this,” Chuck offered, his eyes not moving from where the ice pack lay.

“We need a ride home,” Y/N said.

Dean was shaking his head before she finished the sentence. “No, I’m fine to drive.”

“You must be outta your mind,” Gabe rolled his eyes.

“No one is touching my Baby,” Dean groaned, pushing himself into a sitting position.

Y/N huffed. “Dean, c’mon, you can’t even sit up properly. Someone can give us a ride home and pick us up in the morning.”

Dean grumbled the entire time everyone else discussed things. Finally Gabe was roped into driving the lovebirds home, taking the opportunity to duck out on the cleanup early.

He dropped them off at Dean’s apartment after a short drive and an even shorter argument between the men about whether or not Gabe was going to see where Y/N lived.

Gabe didn’t get out of the car, still a little sore from losing the argument to Dean. Y/N helped Dean out of his seat after getting out herself. Once they were on the sidewalk, she turned back to Gabe and smiled. “Thank you. We’d be really behind the eight-ball without you.”

“Whoa, let’s not get crazy here, doll. I just wanted to get out of cleaning.”

“You can’t pull the wool over my eyes, Gabe—you’re a good egg.”

“Whoa!” Dean interjected. “Let’s not get too crazy here.”

“Listen to Dean-o, doll.”

Y/N laughed. “Good night, Gabe. And, again, thank you.”

Gabriel gave a slight wave before driving off. Y/N wrapped Dean’s arm around her shoulders at that point, walking him towards the stairs. “C’mon, let’s get you taken care of.”

He leaned down to press a soft kiss to her temple, smiling into it. “Lookin’ forward to it, doll.”

* * *

The sun came shining through the window, again failing to fully wake the singer. Instead, she snuggled more into the warmth that she was wrapped around.

She heard groaning, which caused her to just nuzzle her face more into the warmth.

“Sweetheart?”

She only panicked a little before remembering how the previous night went. She opened her eyes and looked up into the face of her beau. His green eyes were sparkling in the sunlight that intruded through the window like some trashy romance novel. “G’mornin.” she mumbled, a smile crossing her face.

“Much as I love this, doll, my ribs are killin’ me.”

She leapt off of him, scrambling to get away like her proximity alone hurt him. “Oh God, Dean, I’m sorry!”

He sat up—with just a little bit of effort—and placed his hand on the back of her neck, pulling her close. “It’s worth it,” he grinned before pressing his lips to hers.

It started out slow and sweet, but then his tongue rolled along her bottom lip and something snapped.

Before she knew what was happening, she was pinned to the bed, Dean resting between her thighs like that was always where he was meant to be. He was resting above her on his right arm, but his left hand was trailing from her knee upwards, squeezing her thigh lightly as he pushed the shirt she’d borrowed to sleep in out of the way.

Y/N’s hands were gripping Dean like a lifeline. One was gripping his shoulder blade, whilst the other held onto the arm he had resting beside her.

Using the hand that had trailed up to her hip, he gripped her hip tightly, pulling them up to slot against his.

She broke the kiss with a moan, and she could practically feel the smirk as his lips trailed down to the junction of her neck. Her nails raked over his back, leaving tiny red marks on his tanned skin in her wake. She breathed out his name, unsure of what she was trying to tell him.

Dean pulled away just enough to look her in the eyes. His heavy breaths were fanning across her face, making it feel even hotter. Then he had to look at her with lust-blown pupils that turned his hunter green eyes nearly black, and she just couldn’t breathe.

“Tell me to stop and I will.”

God, she loved this man.

The revelation didn’t surprise her too much—the feeling had been there for a while now, practically since she met him—but this was the first time she’d actually thought out the words.

And she wanted him.

Her hand trailed up his arm to grip the small hairs at the base of his skull and pulled him down, answering him with a kiss.

Their lips barely brushed together when the phone rang.

Dean’s forehead fell against her as he groaned.

She let the hand at the back of his head cup his cheek as she grumbled, “You should probably get that, Mr. Popular.”

He took a moment, the shrill ringing filling the apartment as he didn’t move.

“Dean?”

“I need a minute, doll.”

Y/N’s cheeks burst into flame. “O-Oh…I, uh…”

He laughed at her response. He leaned down and pressed a kiss to her lips before rolling off of her and out of bed. He trudged over to the door, throwing one last pitiful look at Y/N.

She grinned. “C’mon, they’re obviously not goin’ anywhere.”

“You better not move.”

“Wouldn’t dream of it.”

His lascivious smile turned warm, his gaze softening. “God, I hope not.”

She stood up and padded over to Dean, grabbing his face and pulling it back down to hers. “Wild horses couldn’t get rid of me.”

Their lips connected in a soft, sweet, gentle kiss. She pulled away a moment later and patted him on the chest. “Now answer that phone before they go crazy.”

“Serves ‘em right,” he mumbled against her lips.

She giggled, shoving him playfully away. “Go!”

He sighed over-dramatically as he turned and walked out of the room. “Fine, but I expect a reward when I get back.”

She just smiled as she watched him leaning against the doorjamb.

He picked up the phone, grumbling out a less than polite greeting before the brightest smile she’d ever seen from him spread across his cheeks. “Hey Sammy!”

She began to walk back into the room to give him some privacy when she saw Dean hold his hand out for her out of the corner of her eye. She smirked as she walked up to him, letting him pull her onto his lap.

“Nah, I’m good Sammy. Better than ever, in fact,” Dean leaned in to press a kiss to her throat, his thumb rubbing circles into her hip as he did. She bit her lip, trying not to let any sounds out.

She heard a tinny voice that she assumed was Sammy, but she couldn’t concentrate on anything other than Dean’s lips marking her.

Dean switched between laughing and catching up with his brother and pressing wet kisses to different parts of her neck. She wasn’t sure what she loved more—his smooches or his smile at talking to his brother. He looked so carefree, like he was perfectly content, and she wanted to see that look on his face forever.

Suddenly, he pulled away, causing Y/N to huff in frustration. “No, Sammy, don’t worry about me,” Dean’s brow furrowed together, almost forgetting completely about the woman in his lap. “Stay in California.”

There was a moment of silence where Dean’s jaw ticked. “Well, even if you came out here, I’m busy, Sammy. Save your money. You got a wedding to pay for soon, don’t you? Jess is worth more than me, c’mon…”

Y/N’s fingers carded themselves through Dean’s short, dirty blonde hair, trying to soothe him.

He shot her a grateful look, pulling her a little bit closer. “I’m sorry I had to miss Easter, Sammy, but, you gotta understand…yeah, I know. I promise, I’ll try to get out there for your birthday, alright? …I’ll talk to you however I want, I’m your big brother!”

Y/N leaned down, kissing his cheek, his scruff bristling against her lips.

“I’m sorry, Sammy. Trust me, I wanna see you again, but the club’s been so busy lately, and…wait, w-what’d Bobby tell you?”

Y/N froze at that, but Dean continued. “Y-Yeah, he did come by last night…”

There was a terrible moment of silence before he sighed heavily and fell back in his seat. “Yeah, of course that’s what he told you.”

Y/N searched his face for any indication of what was going on.

“Yeah, she’s…nice.”

A grin slowly made its way across her cheeks.

Dean refused to meet her eyes as the blush across his cheek darkened. “Really nice, alright? Don’t you have better things to do?”

Y/N leaned down, pressing a kiss to his cheek.

“Yeah, I like her…a lot…shut up!” Dean growled, the blush just getting redder and redder.

Y/N giggled at that, and she heard the tinny voice get a little louder.

“Yeah, she’s here, which is why you need to shut your cakehole. I’ll call you later, alright?”

All she heard was laughter coming from the other end of the phone as Dean hung up. He then turned to Y/N and grumbled out “You didn’t hear anything.”

She shook her head, completely serious. “Not a thing.”

He narrowed his eyes. “I’m serious.”

She pressed her lips together, trying to hold back her laughter. “If it helps, I like you a lot too.”

He groaned, which she cut off with a quick press of her lips to his. “I’m gonna kill him,” he mumbled when she pulled away.

She smiled at him, pressing another kiss to his jaw. “You seemed to be having fun. Do you see Sammy often?”

His expression darkened. “No. He doesn’t know that I work for Crowley. I can’t…I can’t let him know.”

Y/N wrapped her arms around Dean’s shoulders, pulling him towards her. He rested his head in the crook of her neck, the arm that had been holding the phone was now resting on her knee.

They sat in silence for a little while, simply enjoying the other’s presence. Finally, Dean said quietly, “I want to spend holidays with him.”

She squeezed him a little tighter. “Why don’t you? I’m sure he’d love ta have you visit him.”

“I don’t want to mix him up in this.”

She ran her fingers through his hair again, pressing a soft kiss to his forehead. “So, what, you’re just never gonna see him again?”

He sighed heavily. “…‘til we get free of Crowley, I can’t take that chance.”

“Dean, he’s your brother. You can’t just ignore him forever.”

His grip tightened. “He’d understand if he knew.”

“Then tell him.”

“Sammy’s a lawyer—he wouldn’t just let it go, he’d try to save me.”

“Why not let him?”

His jaw clenched and his eyes closed. “You know what Crowley’d do to him,” he ground out.

She let her head rest atop his. “I know. I’m sorry. I won’t bring it up again.”

He pressed one more kiss to her collarbone before pulling away. He cupped her cheek with the hand that had been resting on her knee and rubbed his thumb over her cheek. He gave her a small smile before kissing her softly.

Y/N patted his chest before heaving herself off of his lap. “C’mon, you need to get started on breakfast if you wanna eat before Gabe gets here,” she said as she held her hand out, beckoning for him to follow suit.

He rolled his eyes playfully. “Why do I have to cook?”

“Well, I need to make sure you can cook before I decide whether or not to keep ya.”

“Well then!” Dean took her hand as he hopped up from the chair. “If that’s all I gotta do to win you over, get ready to eat the best meal of your life!”

She smiled and followed him, only releasing his hand when he started cooking.

As she kept him company in the kitchen, she couldn’t stop thinking about the phone conversation. In fact, it stayed at the forefront of her mind for the rest of the day.

* * *

She had returned to her hotel room that night. Dean had asked her back to his place, his intention to continue from where they left off that morning clear, but she had been thinking.

Instead, she’d leaned over and pressed a lingering kiss to Dean’s confused face before exiting his car. She didn’t look back at him as she walked to her room, not even when she got to her door to give him a wave, let him know that she was safe. She knew that if she looked back at his jade green eyes, she’d be lost.

She put her bag down by the door, kicked off her shoes, then leaned back against the door. She took a deep, shuddering breath, closing her eyes as she did so.

Finally, after gathering her strength, she dug through her laundry, pulling out a small card. She then sat down on her bed and picked up the phone. She gave the operator the number on the card, and tried to remember how to breathe as she waited to be connected.

Finally, the line clicked, and she heard a gruff, sleep-filled voice mumble out, “Hello?”

“Um…A-Agent Singer? This is Y/N Y/L/N, from…from Crowley’s.”

She heard shuffling, and his voice sounded much more awake now. “Wait…the singer? Dean’s Y/N?”

“Yes sir.”

“Wh…Why are you callin’ me?”

“Because I…I want to meet.”


	12. Chapter 11

She didn’t sleep that night. When the sun finally rose a few hours later, she slipped into some comfortable clothes, and began walking the six miles from her motel door to the diner.

She pushed open the door a few minutes after they opened. There was an older blonde woman behind the counter, who gave her a polite smile as she walked in. “Take a seat anywhere, honey—I’ll be right with you.”

Y/N thanked her and took a seat in the booth towards the back, hiding away from the wall of glass that revealed the patrons to the street. The booth’s vinyl was a little battered, but still shining brightly in the morning sun. The laminate countertops and checkered linoleum floor were spotless for a moment before the breakfast patrons came in, and everything felt a little unreal because of it.

The woman walked up to her, a tired smile on her face. “Hey darling—what can I get ya?”

Y/N asked for some water, unsure if she’d be able to keep anything more substantial down.

The waitress was gone and back with her water within moments. She then looked over the shaking singer. “You sure I can’t get you anything else?”

“I’m, um…I’m waiting for someone.”

“…alright. I’ll come back later, then.”

With that, she was left alone. Y/N didn’t take a drink from her glass, merely stared at it as she waited.

This was the right decision, right? If she did this, Dean would be happy. He could see Sam and, when Sam got married, he could go to the wedding, see his nieces and nephews, everything.

As much as Dean tried to play it off, she knew that, deep down, he was a family man, that his family mattered more to him than everything.

So, if she did this, she wouldn’t just be able to help him see his brother again, but Agent Singer, too. She still wasn’t sure how they knew each other, but she knew how Dean felt about the older man.

Y/N hadn’t ever really had a family before Crowley’s, as strange as the thought was. She’d been on her own so long that, honestly, it would only be them that would be sad if Crowley did anything to her. And, for the chance to free them all, it _was_ worth it, right?

The bell over the door tingled, but Y/N had hidden herself away in the back of the diner, so she couldn’t see who entered.

“Hey Ellen.”

“Howdy, Bobby. Been awhile.”

“Has a young girl come in here? Y/H/C hair, Y/E/C eyes?”

The woman—Ellen, it seemed—chuckled. “She’s a little young for ya, ain’t she, Bobby?”

“Nah, it’s business.”

“Sure a lot-a fellas would love your business, then. She’s in the back.”

“Thanks. Oh, and, Ellen?”

“I know—never saw either-a ya.”

There wasn’t an answer, just the sound of heavy foots walking towards Y/N.

Agent Singer didn’t say a word as he removed his hat and coat before taking a seat across from her. “You eaten?” he asked.

She shook her head.

He sighed. “Figured. You didn’t sleep neither, did ya?”

She shook her head.

He looked annoyed, but didn’t press the issue. They sat in silence for a moment before he spoke, “What made you change your mind?”

Y/N gulped. Her throat felt dryer than the Sahara, but she also felt like vomiting, so the water stayed on the tabletop. “I…” she tried, closing her eyes. “Dean missed Easter. He’s gonna miss Sammy’s birthday, too.”

“Balls,” He sighed quietly. “You love ‘im, don’t ya?”

Y/N flushed, but nodded.

“He know?”

“I…I haven’t _told_ him yet. How do you tell someone something like that? How do I even know that this is love?”

“Does he know that you’re here?” Bobby sighed.

Embarrassment became her primary emotion, and she covered her face. “Oh God.”

He chuckled. “I’m gonna guess no.”

She shook her head, trying to physically shake off her embarrassment. “No. I thought it best he didn’t know just yet.”

“Good,” Agent Singer nodded.

Ellen came by then, bringing a plate of eggs and bacon for the FBI agent and a muffin for the singer.

Y/N tried to return the muffin, but Ellen just stared her down. “This one’s on me, honey. Please, eat something.”

The younger woman nodded slightly and held the muffin, taking the smallest bite possible if only to please the older woman. Ellen smiled, thanked her, and walked away.

Agent Singer was practically halfway through his breakfast, scarfing it down like he would never see food again. He looked up at her, putting his knife and fork down, linking his fingers together on the table in front of him. “Well, you know that we could use your help. Obviously. But I need to make sure that you know what you’re gettin’ yourself into.”

She closed her eyes, taking a deep breath. “Will…Will Dean be safe?”

He shifted in his seat. “I can’t promise that.”

Y/N sighed, letting her head fall into her hands.

“I can’t promise that, but I can promise that I’ll do everything I can to keep him safe,” Bobby’s tone made her look back up at him. The determination practically shined in his brown eyes, and she felt a little better.

“All that matters is that Dean is safe. If you can keep him safe, I’ll help,” she spoke softly, like the words hurt to say.

He nodded.

She looked up at him. “So…what happens now?”

He sighed, leaning back a bit more into the booth. “Well, you can’t change anything about your life. Do what you normally do. Can’t raise suspicion.”

“Okay…” she fiddled some more with her muffin. “What about…what about Dean?”

“Well, obviously, you can’t tell him ‘bout this.”

She sighed heavily, running her hands over her face. “What am I doing?” she mumbled, more to herself than the man sitting across from her.

“Look, if you wanna help Dean, this is the best way to do it. Just…just keep an eye out for anything, any hard evidence you can find around the club. Records, preferably, of how he cleans his money or where he gets it or where it goes. And we can meet here. The Roadhouse is safe, no one’ll bother us here.”

Y/N rested her head in her hand. “God, how did I end up here?”

Agent Singer’s hand closed around hers, causing her Y/E/C eyes to snap up to his deep brown ones. He seemed to struggle for words, the fear that he was losing her and her cooperation practically radiating off of him.

She gave him a soft smile and patted his hand with her free one. “It’s fine. Still helpin’ ya. Just…two years ago, I was homeless and no one cared. Now…life is strange,” she shrugged.

He relaxed a bit at that, letting her hand go. With that, she picked up her bag and began getting up. He frowned, pointing out that she didn’t eat.

She answered with a humorless laugh. “I’m still a little sick, I guess. I need to get back to my hotel if I wanna hope to get any sleep before the show tonight.”

He nodded. “Okay. I’ll meet you here in a week, alright? And don’t call me from your hotel room again—use a payphone far from your hotel, Dean’s place, the club, anywhere you normally go.”

She gripped her bag a little bit more, her knuckles turning white. She gave a curt nod and turned to leave. She thanked Ellen as she walked out, and began the trek back to her hotel room.


	13. Chapter 12

Even though she's used sleep as an excuse to escape from the meeting, she'd not been able to rest for more than twenty minutes at a time.

When Dean rolled around at noon as he usually did, she would've been surprised if she'd slept an hour in total.

The moment she sat down in the car, Dean's hands were cupping her face, forcing her Y/E/C eyes to meet his green ones. “Hell, did you get any sleep last night, doll?”

She shook her head, taking Dean's hands in her own. “No, but I'm fine. Was just thinkin’, that's all.”

“Thinking?”

“Yeah.”

“That can't be good.”

She laughed at that, leaning forward to press a kiss to his lips. “Nothing too terrible, I promise.”

He looked unconvinced.

She let her jaw hang uselessly for a moment before speaking again. “I know I was acting weird yesterday, but you need to know that it wasn't your fault. You didn't do anything.”

He remained unconvinced. “I…I didn't do anything?”

“No, nothing, Dean.”

“Son of a bitch,” he muttered under his breath, running a hand over his mouth in frustration.

“Dean, I swear, I—!”

The roar of the engine cut her off and he refused to look at her any more. He didn't look at her as he pulled away from the curb, nor during their commute to the club, nor when they finally arrived. He didn't take her hand as they walked in, barely said a thing to anyone, and ran back into the dressing room the moment he could 

Castiel sent a confused look from his post at the bar, which Meg quickly vocalized. “What's his problem?”

Y/N sighed heavily. “Nothing too bad, hopefully.”

That was enough to silence them, though they remained dubious (as made obvious by the frown on Cas’ face and the eye roll from Meg).

Gabe and Chuck filed in, commenting on the lack of their pianist, but otherwise happy to give him his space.

It wasn't until the doors opened and the set began that things took a turn.

Dean hit the wrong note in the first bar of their first song. In fact, for the entirety of that first song, it was as though he had never seen a piano before.

After that disaster, Y/N pulled Dean aside, leaving Gabe and Chuck to try and entertain by themselves. She had to practically drag him backstage and, the second they were alone, she whirled around on him. “What's wrong?”

“I'm fine. Ribs hurt a little, but that's it.”

She took his hands hands in hers. “Didn't bother you last night.”

“Well, I’m sore from playing yesterday. Obviously.”

“Don't feed me a line, Dean. If you don't wanna talk about it, I won't make you, but, please,” she begged. “Don't make me watch you get hurt again.”

His jaw clenched and she worried that she might've said the wrong thing. Then he simply gave her a curt nod, and they headed back out.

For the rest of the evening he didn't hit another sour note, though he never played to his full potential. Worried looks were exchanged all throughout the night between not only the band members, but every member of their little family.

At the end of the night, they all separated as though they were strangers with not a word exchanged between them.

The boys were out within minutes, each claiming to have an appointment they simply could not miss. The bartender and waitress had disappeared after they had said their good evenings, eager to leave the awkward atmosphere that had permeated through everything all night.

This left only the pianist, singer, and bouncer.

“If you'd prefer, I can walk back to my hotel tonight.”

“No, it's fine.”

Benny had thrown a pitying look to the singer at that. She had responded by leaning down to press a kiss to Dean's temple (for he still had yet to look her in the eye) and walking off to the dressing room to change.

She was in and out rather quickly, eager to return to Dean, even if he was acting like a ninny. She walked down the empty, silent hallway, stopping before she went back into the main room. Her eyes didn't leave the other end of the hall, but her mind wandered.

It wandered down the pristine floors, down and around the corner to the beautiful dark oak doors that marked the entrance to Crowley’s private office. She imagined opening the doors, revealing a torture chamber, with flames dancing around and filled with the screams of his victims.

That image snapped her out of it. She shook her head, as though she had to physically get rid of the image.  _ Another night, _ she decided.  _ I can't do this all in one day. _

With that, she silently pushed open the door to the main room.

At the bar sat Benny and Dean, unmoved from where she had left them. The bouncer was facing her direction, but his clear blue eyes were focused on his friend. They were speaking just quietly enough for her to be unable to make out what they were saying. Concern was etched into Benny’s features, and it worried her.

She tiptoed towards the friends, hoping to eavesdrop just a bit on their conversation.

Unfortunately, the moment she moved, Benny’s gaze found her. He bowed his head in a silent greeting before turning back to Dean. “Speakin’ of your girl.”

Dean turned to face her, a storm of emotions flashing over his face much too quickly for her to catch.

She smiled warmly, wrapping an arm around Dean's shoulders when she was close enough. He didn't lean into her, and she tried not to worry about that. “Talkin’ ‘bout me? Well, Benny, you know that Dean’s a filthy liar.”

“He said nothin’ but good things.”

“Which only proves my point.”

Benny laughed at that as he stood. “Well, brother, I leave you in good hands.”

“Sure you don’t wanna come back to mine for a nightcap?” Dean tried. “We haven’t seen each other outside-a Crowley’s in a long time.”

Benny frowned, seemingly annoyed with his friend. “Think I’m not the one you should be talkin’ to. Rain check, brother.” With that, he turned to Y/N, wished her a good night, and headed for the door.

Y/N sighed heavily as Dean stood, throwing back the last of his whiskey as he did so. He hadn’t looked at her yet. 

She huffed in annoyance. “Would you prefer I take a cab?”

“Whatever you’re comfortable with,” he muttered into his glass.

She crossed her arms over her chest. “Okay, what did I do?”

“Nothing.”

“Then what’s got you so wacky?”

He finally turned to look at her then, his eyes wide. “What?”

“You’ve been in a mood all day. You won’t talk to me or anyone, and you’re worrying  _ everyone. _ Either talk to  _ somebody _ about it or stop being such a fat-head!”

His hunter green eyes were open enough to nearly pop out of his skull.

Silence hung over them. After letting it rest for a moment, Y/N put her head in her hands. “Dean, I’m sorry. I’m sorry for whatever I did, for—!”

“You’re not mad at me?”

Now her eyes widened. “What? Why would I be mad at you?”

A slight smattering of pink made its home on his cheeks. “Well…yesterday, we were gonna finally…have a bit of fruit, then Sammy called, and, for the rest of the day, you were off. You didn’t join us in making fun of Chuck when he tripped over his bass and nearly fell off the stage, just helped him up. You were quieter than usual and…and you went back to your motel. I thought I had…pushed you too far.”

Watching him so worried, so nervous, so not-Dean was doing things to her. The man who was so confident—bordering on cocky—was suddenly like a child in front of her, afraid that he had done the wrong thing and desperate to make it up to her.

She took his hand in hers, squeezing it gently. “I’m so sorry to worry you, Dean. I was just… _ you _ didn’t do anything wrong, I swear.”

He pulled her into a tight hug, as though she was going to try and run away. “We can wait forever, sweetheart, I promise.”

She shook her head (as much as she could with her face buried in Dean’s chest). “I was simply in my own head too much yesterday. I’m sorry I didn’t notice. You did nothing wrong. I promise I’ll try not to make you wait too much longer.”

He pressed a firm kiss to the crown of her skull. There was a long, pregnant pause before he spoke again. “Does that mean you’ll come over tonight? I just…I sleep better with you nearby.”

She pulled away, smiling softly. “I’d like nothing more.”


	14. Chapter 13

The first month of Y/N’s attempt at espionage hadn’t gone exactly as they had hoped.

The first time they'd met was exactly a week from their first meeting. She’d told him that she’d yet to find anything more substantial, but had told him the story of the night she had found out how Dean “helped” Benny.

He had begged her to get into Crowley’s private office, a statement that sparked off an argument that would’ve devolved into a shouting match had Ellen not walked by and smacked the older man upside his head.

“What do you expect, Bobby?” she grumbled, handing the young singer some eggs and bacon and the federal agent nothing. “It's not like she's got the keys to the kingdom.”

Bobby frowned, but couldn't argue with that. He had already brought up the idea of getting closer to Crowley, but Y/N had told him  _ exactly _ what he could do with that idea, and the subject was swiftly dropped.

In the end, they separated, the singer frustrated and the federal agent disappointed.

And Y/N had been reticent to meet as often as they did. She'd tried to talk Agent Singer into meeting every other week or possibly even once a month, since the trickle of information had been stoppered. She had practically heard a gasket pop, and that idea was shelved as well.

She was worried, though. Ever since meeting with Agent Singer, Dean had yet to invite Y/N back to his place. Every night, he pressed a soft, chaste kiss to her cheek and wished her sweet dreams, and then drove off.

She’d then trudge up the rickety stairs to her room, frowning. Of course he’d take her saying that he hadn’t pushed her into anything as the exact opposite of what she said. But she hadn’t had a good excuse for acting the way she had, and Dean had practically gift-wrapped that one for her.

Unfortunately, it was still a lie. She was just as ready for Dean to be her first a month later. However, any time she tried to broach the subject with him, he’d just given her that stupid smile that never failed to make her weak in the knees and simply pulled her in for a hug, telling her that they didn’t need to rush.

So, here she was, a month later and frustrated on several fronts.

Life at the club hadn’t changed too drastically. Meg still supplied Y/N with the appropriate gossip (which, if important, she’d pass on to Agent Singer); the band still drew in enough crowds to fill a lesser place for a month; and the group still communicated mostly through light-hearted insults.

Crowley was still hidden away from the rest of them, rarely showing himself. His mere presence seemed to suck any life out of a room, and she thanked her lucky stars that they didn’t often cross paths. It was hard enough when he made his rounds during business hours, schmoozing and making shady deals with faceless patrons.

But, at the end of every night, Dean would go sit at the bar with whoever was still there (usually Benny, Castiel, and Meg, though it varied night to night), and Y/N would try to gather up the courage to get into Crowley’s office.

Or at least make it down the hall.

Or even look in the direction of Crowley’s office.

Baby steps.

* * *

The night of May thirtieth was exactly like all the others. The band crooned, the booze poured, and a great time was had by all. Benny and Dean helped a particularly drunk patron out to the curb to hail a cab whilst Chuck and Gabe made their home at the bar with Castiel and the girls.

Gabe had made a joke about Y/N sitting on his lap, but a swift glare from Castiel ended that. “Whoa, easy there, brother,” Gabe chuckled.

Meg had rolled her eyes and Y/N did the same as she laughed. 

“Just because we are brothers does not mean that I will allow you to act in such a manner, Gabriel,” Cas frowned, his low, gravelly voice completely monotone.

“Wait, you two are actually brothers?” Y/N’s head cocked to the side in confusion.

“You didn’t know?” Chuck was incredulous.

“It’s never come up!” she defended.

“Plus,” Meg added, walking behind the bar to join Castiel. “These two couldn’t be more different. Who’d ever think it?”

Gabe raised his glass. “I’ll take that as a compliment, doll.”

Meg clinked her glass with his, grinning. “Take it however you want.”

They all laughed at that. Castiel had even pressed a kiss to Meg’s temple.

The doors opened, revealing Benny and Dean as they entered, both looking a little frazzled.

“The old guy finally get home safe?” Chuck asked.

“It took us twenty minutes to convince him that his taxi driver wasn’t, and I quote, a ‘cock-eyed kraut out to gas us all,’” Dean groaned, taking a seat at the bar next to Y/N.

Benny chuckled as he took another free seat, next to Chuck at the other end of the bar. Castiel was on it the moment they walked in, and Benny was greeted with a full glass of whiskey upon his seat. Benny thanked him before drinking from it like a man who hadn’t seen water in days.

Castiel turned to give Dean the freshly-poured drink a moment later. Dean thanked him gruffly and turned to his girl. “And you ain’t even changed yet,” Dean groaned, running a hand down his face in frustration.

Y/N looked down to see that, damn it, she hadn’t changed yet. “Oh, I’m sorry! We just got distracted! I’ll be back in a jiffy!” she practically dropped her glass onto the bar, gave Dean a quick, close-mouthed kiss, and hustled off to the back room.

“Hurry back!” he’d shouted after her. There was a beat of silence after that, but, before she shut the door to the hallway behind her, she heard a shout of pain from someone (probably Gabe), followed by laughter.

She was in and out in a moment, faster than usual. She was about to run out and join her friends once more when something caught her eye.

The way the hallway leading to the part of the nightclub she rarely visited worked was simple: it was straight down the line, with exposed brick making it feel claustrophobic. Then, at the very tail end of the hall was a ninety degree turn to the left, back towards the club. At that turn lay Crowley’s office. Y/N had only walked down to that end of the hall once and had chickened out long before the idea of actually trying the doors entered her mind.

Tonight, though, there was a sliver of light stretching around the corner, drawing her eye.

She had never seen the light like that. It was like a call, a message:  _ Y/N, get your ass over here. _

She took a deep breath, closing her eyes as she did. When they opened again, she was walking towards the source, praying that everyone would be too occupied with each other to notice her extended absence.

Her footsteps made no sound as she tip-toed down the hall. Usually, she couldn’t keep her shoes quiet on the hardwood floor, but, without trying, her shoes suddenly decided to cooperate with her. A part of her wondered if it was the walk of a dead man, and the thought gave her chills.

She peeked around the corner and through the slit caused by the open doors, looking for any other living creature. There were none.

She took another deep, shuddery breath, and pushed through the door.

The inside of Crowley’s private office was simultaneously nothing and exactly like she imagined. A juvenile part of her assumed it to be a throne room surrounded with flames and the cries of his victims. In actuality, it was a room that oozed comfort and intimidation. Everything had a sharp edge and was either red or black. His dark mahogany desk reminded her of a war table--large and with many sinister bits and pieces covering it. The only plush thing in the room was his chair, which had a high back and was covered in a deep red felt and looked comfy enough to sleep in.

She walked around to the back of the desk, her Y/E/C eyes scanning the desk for something,  _ anything _ noteworthy enough to jump out at her.

Some of it was in code and there was no way she’d remember what they said. She knew she couldn’t take anything in case Crowley noticed something was missing. He didn’t seem the scatterbrained type, so she doubted that he often lost important documents.

Here was a golden opportunity, and here she was, woefully unprepared.

She chewed her bottom lip in contemplation, deciding to just try and figure out as much as she could and then come back another night with perhaps a notepad or something to take notes on.

She picked up a few things but was careful to leave every bit of paper exactly where she’d picked it up once she was done. She saw the name of a bank appear over and over again, and that would be easy to remember. It was a lead, which would be more than she’s given them so far. She was actually happy, actually proud of herself. She had been so afraid, so petrified, but she could do this. She could save Dean.

Then came a single sentence that turned her blood to ice.

“What the hell are you doing?!”


	15. Chapter 14

There was no getting out of this. Nope, she was definitely dead.

Her Y/E/C eyes trailed slowly up to the intruder—the other one.

Standing in the doorway was Gabriel, his face set in a rare frown. His right hand was on the door, holding it open as he held his left hand out. He looked around one more time before he whisper shouted, “Get over here!”

She ran over to him like the floor was made of lava, trying to touch it as little as possible.

Once she was close enough, Gabriel grabbed her and yanked her to him with a strength she would never have thought possible of the drummer.

“What the hell are you doing?!” he hissed once more, shutting the door quickly but quietly.

“I, uh, I was jus—”

“Are you crazy?! What if it was someone else who caught you?!” he growled, dragging her away from the office by her wrist.

“Gabe, it’s not—”

“What were you thinking?  _ Were _ you even thinking?!” he grumbled on rhetorically.

Finally, she had enough and planted her feet, She was not going to be yanked around like a child. She had had a moment in that office, a moment where, finally,  _ finally _ she had stepped up and done something other than just survive.

And, you know what? Fuck Gabe for ruining it.

When he felt her stop, Gabe turned to her, his hazel eyes blazing. He opened his mouth to, she was sure, yell at her some more when she stopped him. “Why don’t you close your head, Gabe?!”

His eyes widened, and his primary emotion became surprise.

“You don’t know a damn thing that’s happenin’, alright?! And you have no right to drag me around like I’m your property!” she wrenched her arm away from Gabe’s grip, her face getting redder by the second.

He laughed. A full-on laugh that bubbled up from his stomach and made him throw his head back.

This only enraged her further. She stomped her foot, like a child. “Don’t laugh at me! I’m being serious!”

Gabe calmed down enough to throw an arm around her shoulders, pulling her into a hug. “Oh, doll,” he got out between laughs. “You are one-a kind.”

She pulled out of his grip, ready to throw more verbal jabs at him when Gabe held up his hand, stopping her. “Fine. I’m sorry I tossed ya around like that. I had no right to. I was just scared for you.”

“Funny way-a showin’ it.”

He shrugged. “I’m a funny guy.”

She sighed heavily, her jaw ticking in irritation.

There was a beat of silence before he turned to her. “So, you gonna tell me what you were doin’ in there?”

She swallowed thickly, unsure of what to say, how to even approach the situation. “The, uh...the door was open, and I was curious.”

He rolled his eyes. “Don’t take me for a sap, doll.”

Her Y/E/C eyes met his hazel ones, and his eyebrow rose. How he could tell her with a single eyebrow to start talking was beyond her, but that’s what he was doing.

She sighed heavily. “I can’t tell you, Gabe.”

He nodded, taking a moment before speaking again. “You’re doing something you shouldn’t be doing.”

She didn’t answer.

“You’re helping the g-man, the one Dean knows.”

She didn’t answer.

He laughed without humor. “Are you insane? You saw what happened when Dean just said hello to the guy!”

“Dean’s the reason I’m doing this, Gabe!”

“Really? No other reason? Not to get yourself out of here or undo whatever is it that got you in here?” his voice raised just slightly, almost yelling.

She shook her head. “I...he offered to help me with my charges, but…”

“Charges? What’d you do?”

She snapped. “Well, what’d you do, huh?”

Gabe laughed at that. “Nothing. It’s what Cassie there did.”

“Cas?”

He shrugged. “Cas buncoed Crowley, got himself in deep, and I joined the band to keep an eye on my baby brother. See? Not so hard to share now, is it?”

“Wait, so you’re not in debt to Crowley?”

“What can I say, I’m smarter than the rest-a you mugs.”

“So...you can just leave whenever you want.”

“No I can’t,” he frowned, like she was crazy. “Not until Cassie is free and clear.”

She smiled softly. “Gabe, you’re...different than I thought.”

“Look, he’s family. I’m still the same, self-centered schmuck you know and love. Now, time to share, alright?”

Y/N let herself fall back against the wall, leaning all of her weight on it. Her head fell back as well, resting it there. She licked her lips and said simply, “I robbed a bank.”

He laughed. “No, you didn’t.”

She shrugged. “Yes, I did. I was on the nut and worked at a bank. It’s not important.”

“Sounds pretty important, doll,” Gabe laughed. “Wow...you are different than I thought.”

She scoffed. “Touché.”

Gabe took a moment more before speaking again. “This is some bad business, Y/N, and you know it.”

She nodded. “I know. But...no one deserves to be here. And I ain’t got anybody outside the club who’ll miss me if...if the worst happens.”

The drummer sighed heavily, running a hand through his hair. “Alright, alright...you know I won’t snitch on ya.”

She thanked him, relief settling on her.

“Don’t thank me. Tell that hombre of yours what you’re doing.”

“Tell him? Are you insane?”

He shrugged. “Don’t see how you’re gonna hide this from him for long. Better to tell him now, get it over with.”

She pushed herself off the wall with a huff, done with the conversation, and she told him as much.

“C’mon baby doll,” he walked quickly to catch up with her. “You know I’m right.”

Before she could say anything, the door to the front room opened, revealing a frowning Dean Winchester. His emerald green eyes found the other two standing in the hallway. He laughed, sensing the tension. “Hey, you trying to steal my girl again, Novak?”

Gabe was immediately on form, as though the last few minutes hadn’t happened at all. “You just wait, Dean-o. I’m not even trying yet.”

Dean walked over to Y/N, placing a hand on her shoulder and pulling her close. He smiled tightly. “Well, you’ll have to try another night. I’m exhausted, and I still need to get her home.”

She wrapped an arm around Dean’s middle, studiously ignoring the knowing look Gabe shot her, trying to hide in her boyfriend.

Gabe said his goodbyes, sauntering out to join the rest of the crew at the bar.

As soon as they were alone, he pulled her into a tight hug. She hugged him back as tightly as she could, the emotions of her evening catching up to her. Before they fully pulled away, Y/N grabbed Dean by the back of his neck and pulled him down into a kiss.

He searched her eyes when they pulled away.

She just smiled and shrugged. “Everything’s fine. Let’s just go home.”


	16. Unfun Author's Note

Hey guys!

For those who don’t know, I’m moving this weekend, and I’ll be without internet until late Sunday. Even then, I won’t have time to sit down and post and finish up the next chapter of [Good To You](http://quiddy-writes.tumblr.com/tagged/gty) in time.

That means that, for the first time since I started posting, I’m gonna have to miss a week of Good To You.

I _sincerely_ apologize for that, guys. I promise it’ll be back on schedule next week, but I just won’t have time for it this weekend.

Thanks y’all for being so understanding! I hope everyone has a great weekend.


	17. Chapter 15

**Notes for the Chapter:**

> Okay, first of all, I'm so incredibly sorry that this is up a day late. Almost two (I'm posting this kind of close to midnight). Long story short, I had plans this weekend for getting this chapter up which got bent over a table, so, yeah. Then, to add a cherry on top of a pretty shitty weekend, I got sick. But, FINALLY, there's internet at the new place, so I can post things once again! Huzzah! Hope this was worth the wait, and thanks so much for your understanding and patience! I love you all.

Dean didn’t bring up the weird situation he’d found Y/N and Gabe in, but she knew it was eating at him.

He was just a bit more irritable, and was often found glaring daggers at the drummer of the course of the next few days. She sometimes worried that he would leap across his piano and start beating the drummer, but it never got that far. The closest he got was clenching his fists when a joke of Gabe’s made her laugh.

She wished that she could just explain everything to Dean, but Agent Singer had been very clear: tell no one. She’d seen her life flash before her eyes when she’d told him about how Gabe how found out. Had it not been for Ellen, a part of Y/N thought that she’d end up on the evening news as a missing person.

He’d only calmed down once she told him about the bank. His dark eyes had lit up, and a smile spread across his face. It was awkward, like it didn’t happen often. He seemed to catch himself, the usual gruff exterior returning quickly. He’d thanked her and asked her to continue her good work.

She’d left the diner with a little spring in her step that day.

A spring that was long gone by the time she had stepped foot in Crowley’s.

Dean had been terse with her since he had found the drummer and the singer in the hallway. Whenever she’d spoken to him, telling him that it was nothing, that nothing had happened, he’d simply smiled tightly and told her that he believed her.

She wasn’t sure if that was true or not.

She and Dean started drifting apart. She stopped asking about staying at his apartment overnight and  they stopped joking around and spending every moment together. The entire tone of the band’s friendship turned dour, and their performances suffered for it.

After the third day, Meg pulled Y/N aside. She asked, in the nicest way possible, what the hell was going on. Y/N had smiled sadly and softly and shrugged.

Meg never got a straight answer.

* * *

A week later, Y/N stood in the hallway once more, alone. She hadn’t had a chance to go back to Crowley’s office and things had been quiet. At least, quiet enough for Y/N to not hear anything of worth to report.

Honestly, though, she hadn’t really been trying. She was focused solely on her band.

Chuck had shrugged and nodded when she had spoken to him about it, acquiescing that he’d noticed the shift in their dynamic too. He’d suggested talking to Gabe himself, but she’d stopped that.

Last thing she needed was yet another person in on her secret.

Instead, the tension festered like an open wound between them all.

The door opened with a creak as Y/N finally threw her coat over her shoulders. She turned to see Gabe closing the door behind him as he entered. His hazel eyes glared at her, narrowing ever so slightly.

She squared her shoulders and turned back to the mirror she was standing in front of. She busied herself by making sure she looked good as she spoke as nonchalantly as possible, “What can I do ya for, Gabe?”

“You have to tell him, doll.”

“No idea what you’re talkin’ ‘bout,” she sighed lightly, turning towards Gabe. She smiled insincerely. “Excuse me, but I’m going home.” She said as she tried to breeze past him.

His hand shot out and grabbed her arm, holding her in place. The glare he gave her would’ve killed a lesser man. “You tell Dean about this thing, or I will.”

“You shut your face,” she hissed quietly. “This would kill Dean, and you know it.”

He rolled his eyes. “Yeah, well, you should’ve thought ‘bout that earlier.”

She wrenched her arm from him, tilting her chin up in defiance. “Don’t you dare. He’s the whole reason I’m doing this.”

Gabe shook his head. “Yeah, yeah, I know…just…you gotta promise me you’ll be careful. You don’t meet with him a lot, do you?”

“Every Friday morning.”

He laughed humorlessly. “Well, when you see him tomorrow, tell ‘im I said hi.”

She huffed out a laugh at that. “I’m sure he’d love to talk to you, too.”

“Thanks, but no thanks.”

“Worth a shot.”

Gabe wrapped an arm around her shoulder and pulled her close for a hug. “You be safe, okay doll?”

She patted his arm before pulling herself from his embrace. “You’re a real good egg, Gabe.”

“I know.”

She bid him goodbye before she walked out the door and into the hallway.

* * *

“Morning, sweetheart!”

Y/N smiled warmly at Ellen as the singer walked into the small diner. “Good morning, Ellen. It’s lovely to see you.”

Ellen turned to her cook and barked, “Y/N’s here: her usual, Ash!”

Ash, a man who looked like he camped out at soup kitchens, shouted from the kitchen, “Got it!”

Y/N thanked Ash as she walked over to the table in the back, taking her usual seat. By the time Agent Singer arrived, Ellen’s daughter, Jo, was dropping the small plate off. The singer thanked the waitress. Jo had only begun working this shift in the last week or two, so Y/N wasn’t as close with her as she was with Ellen, but she seemed nice enough. In fact, the moment she saw Agent Singer sit down with her, Jo had immediately begun to be infinitely nicer to her, not that she had been rude before. She must’ve known that working with the feds meant she was living on borrowed time and was trying to be kind, and Y/N was grateful for that.

Y/N dug into her small breakfast (she was still too nervous at every meeting to eat a full, real meal), getting about halfway through it before he joined her.

He grunted out a gruff greeting. Ellen could be heard yelling Agent Singer’s order out to Ash in a similar manner to how she had a few minutes earlier. Ash was like a culinary magician, because the usual coffee, eggs, and bacon were being brought out by Jo by the time Agent Singer had peeled off his overcoat, hung it up, and sat down.

Y/N and Bobby began discussions. She asked how his investigation with the bank she’d given him was going. He’d grumbled out that banks were so stupidly secretive with their clients’ account information, so it was going to take a little while.

She’d sort of deflated at that. Without realizing until that very moment, she’d hoped that that one bit of information would be enough to take him down, that they would be free and clear.  _ I’m such a sap,  _ she shook her head at her own naivety.

They spoke a little more, but Y/N had little to report, which cut their meeting short.

Agent Singer offered to give her cab fare, make sure she got back to her hazard of a hotel safely. She thanked him, but declined. “I could use the walk. Ash’s tryin’ to fatten me up, I swear!” she’d joked.

Ash had shouted a vague sound of agreement from the kitchen, which made her smile and the other girls chuckle. Agent Singer had eyed her, as he was wont to do, trying to make sure that she was confident in her decision.

She waved them off, leaving Agent Singer behind to finish enjoying his breakfast and ineptly flirt some more with Ellen. She rubbed her hands up and down her arms, trying to get some warmth into them. Even if it was finally June and summer was peeking through, that did nothing to warm her so early in the morning.

She walked the few miles back to her motel, content in the quiet. Not that anything could ever be truly quiet in Chicago. The hustle and bustle of city life made sure that there was a constant symphony of sound underlying everything, and she loved it. It made her feel less alone.

She smiled when she saw her dinky motel’s sign high in the sky, beckoning to her.

A smile that fell when she saw a familiar car sitting in the parking lot, with a familiar figure leaning against it. Her Y/E/C eyes met the beautiful hunter green eyes of her pianist, and he gave her a sarcastic, strained smile. “Looks like you’ve got some explaining to do, huh?”


	18. Chapter 16

**Notes for the Chapter:**

> MERRY CHRISTMAS!! I stayed up until about 3 to write this, because I spent all Christmas Eve playing Overwatch and packing for my trip up north to visit family, rather than the writing I had planned to do. That being said, I can’t wait to see how y’all react to this chapter :D

“Dean,” she began, fully planning to speak more if it hadn’t felt like she’d just gotten a swift punch to the gut.

He shook his head. “Come on, it’s freezin’ out here. Let’s go to your room.”

She nodded and, on instinct, held her hand out for him to take.

He didn’t.

She awkwardly pulled it back, shoving it into her overcoat as they walked up the stairs to the second floor. They walked in silence down to her room. She fumbled with the keys for a moment, her nerves showing as she pushed open the door and walked in.

She heard Dean close the door behind him as he entered, and she walked over to the small kitchenette. “Can I get you something to drink?” she asked, finally looking up at Dean once more.

He was standing still next to the door, his back almost touching it. His jade green eyes were scanning the room. His face fell slightly. “Damn, doll, I didn't know it was this bad,” he mumbled.

She shrugged. “It works for now.”

He locked eyes with her, an apology hidden in his eyes, like he had done something wrong. Then, he frowned, steeling himself. He then turned to the bed and sat down on the edge of it.

She sighed, turning to face him and leaned heavily against the paper-thin wall, her own legs getting too shaky to full hold her up.

They sat in silence for a few more minutes, unsure of how and where to start. Y/N’s eyes traveled over him, looking for any clue he might give as to how much he knew.

“I’m waitin’ here, doll.”

She swallowed thickly. “What’m I bein’ accused of?”

He huffed out a laugh at that. “Forgot you’ve been interrogated before.”

She smiled slightly at that.

He looked up at her. “Well, you aren’t steppin’ out on me.”

She shook her head. “I never could.”

His hand came up to rub the back of his neck, a heavy sigh leaving his plush lips. “You and Gabe weren’t inspirin’ a lot of confidence.”

She shifted awkwardly. “I guess not. I tried to tell ya, though.”

“Yeah, I know,” he conceded.

“Not that it made me look any less guilty.”

He gave a real laugh at that, before the room settled back into an awkward silence. He finally looked up at her, his jade eyes locking with her Y/E/C ones. “You’re not gonna admit to anything, are you?”

She smiled sadly. “Might be how I got into all this in the first place.”

He nodded, a look of acceptance on his face. “Fine. I know you’re working with Bobby. That’s your secret, isn’t it?”

She inhaled sharply, her eyes widening a bit. “Wow, say what you’re really thinkin’, Dean.”

“How long?”

“How’d you find out?”

He ran his tongue over his lips before speaking. “You were takin’ a while to get ready last night. Went back to check on ya, heard you and Gabe talkin’. First, it sounded like you two were going behind my back, but then you started talkin’ ‘bout meetin’ with someone, and I thought...I thought there was another guy I didn’t even know about.”

“Dean,” she began, the need to comfort him beginning to take over.

He avoided looking at her, trying to hide the fact that his cheeks were beginning to pinken. “It drove me bonkers. Dropped you off, went home, and I couldn’t sleep. I knew you were meetin’ him this morning so I…”

“You followed me to Ellen’s.”

He nodded. “The minute I saw you go into the Roadhouse, I knew who you were meetin’. Ellen and Jo and Ash…”

“They’re family too.”

He smiled sadly.

“More family you haven’t spoken to since startin’ at Crowley’s.”

His expression hardened. “But that’s not what we’re talkin’ ‘bout here.”

“‘Course not,” she grumbled.

“How long have you two been meetin’?”

Her eyes fell to the floor. “A month? Month and a half, maybe. Since that night they came to the club.”

He was on his feet and in front of her before she could blink. He reached out to grab her arm, his grip strong, but not painful. His face contorted in worry and his voice was strained when he spoke, “You’ve gotta stop and stop right now. Today was the last time you meet with him.”

She frowned. “No, it wasn’t.”

“Y/N--”

“No, Dean, I have to help him.”

“Are you nuts? Have you thought about what Crowley will do to you?”

“It doesn’t matter. No one outside the club’ll miss me, Dean.”

Sadness tinged his expression. “So our feelin’s don’t matter? Have you thought about how Meg or Chuck or-or the rest of us will feel?”

She gulped, her eyes closing. “Dean, if I do this and it _works_ ? Then I can save you, I can get you _all_ out of there.”

Dean’s other hand came up to cup her cheek. “It’s not worth you dyin’, sweetheart.”

Her eyes opened and locked with his. “‘Course it is, Dean.”

That seemed to send him spinning. His hands fell away and he took a step back, like she had shoved him.

She took the chance to keep speaking. “When was the last time you saw Sammy? And he’s _engaged_ , isn’t he? He’s gettin’ married to this girl, and have you even met her? What about Agent Singer? He’s your family, and you can’t talk to him without gettin’ hurt. Dean, you’re the best man I’ve ever known, and you deserve so much more, and, and if this is the only way I can help you, then--”

“What about what you deserve? You’re the one gettin’ the short end-a the stick here, doll.”

“Dean, what part of ‘no one outside the club will miss me’ did you not get? You’ll all be free to be with your families and-and what about everyone else Crowley ruins? What about those people you and Benny haveta rough up night after night? They’ll be helped, too.”

He ran his hand down and over his face in frustration. “It doesn’t help anyone to lose you, baby.”

She walked over to him slowly, like he was a wild animal. He didn’t move, not to bring her closer nor push her away. Her hand reached out to link her fingers with his, and he let their fingers entwine as they had a hundred times before. “I’m scared, Dean.”

His eyes met hers, and he opened his mouth to speak.

She interrupted him. “I’m terrified of dyin’. Of going to jail. But...you make me brave. I’ve been a coward my whole life--it’s how I’ve survived. But, with you, I wanna be...I wanna be _better_. So you gotta let me do this for you. To repay you.”

He shook his head. “Pay me back by stayin’ alive, doll.”

Her free hand made its home at the soft hairs at the back of his neck, pulling him down into a soft kiss. “Dean, I…” she took a deep, shuddering breath. “I love you.”

His eyes snapped open, surveying her with such a mix of emotions as to be absolutely, frustratingly unreadable.

She laughed awkwardly. “So that’s why I’m doin’ this. I’m selfish, Dean. I robbed a bank to make my life better, and I’m doin’ this because, as long as you’re happy, I’ll be happy.”

“I…” he trailed off, his brow furrowing as he searched for words.

“So,” she pulled herself away from him, putting a full foot of distance between them. “I’m not gonna stop helpin’ him. And I’m not gonna ask you to help us, either. But...this is what I’m gonna do, whether you like it or not. And...and I understand if you can’t be involved...in...in any way.”

He stared at her, and she tried not to falter too much under his intense gaze. Her resolve was iron in this matter, but he might break her if he left, if she had to go on and continue without him. She would let him go if need be, however, if it made him happier.

“God, doll,” he breathed. “What am I supposed to do?”

She felt her eyes burn with tears. “I have no idea, Dean. I honestly don’t know how I’d do in your shoes.”

“That makes two-a us.”

She chuckled at that.

Silence reigned again. She stayed silent, letting him absorb everything that had happened, and waiting on pins and needles for his reaction. Her nerves were raw, and she was terrified of his response. What if he left her? What if he stayed? What if he loved her? What if he didn’t? She wasn’t prepared for anything.

Finally, he spoke. “I need...I need time. To think. To deal with this.”

Her Y/E/C eyes watched him as he began to pace. “Okay,” she agreed quietly.

“I might have to slug Bobby, bringin’ you into this after I told him to stay away.”

“Dean, _I_ called _him_.”

“Yeah, after he showed up at the club,” he shot back.

“I’m not a kid, I can make my own decisions.”

“You’re nineteen. And your last decision ended up gettin’ you stuck at Crowley’s.”

“Wasn’t the worst decision I coulda made,” she frowned, her arms crossing over her chest.

A smile graced his features at that. “Well...I can’t argue with that too much.”

A small sigh of relief left her at that. “Will we ever be…?”

He stalked over to her, pulling her by her shoulders into a bruising kiss.

She gripped his shirt tightly, afraid that this was goodbye. She faintly heard fabric rip under her hands, but she paid no mind.

He pulled away, her following just a moment before falling back onto her heels.

His usual cocky smile was in place when her eyes opened again. “I should probably tell ya that I’m crazy for you too.”

She brightened a bit. “Yeah?”

He shrugged. “Yeah. Can’t believe you haven’t figured that out. I wouldn’t follow just any girl.”

“I’m _your_ girl, Dean. Long as you’ll have me.”

He smiled, pulling her into a tight, bone-crushing hug. “Well then, baby, you’re in for the long haul.”

Her entire body shook as she sighed heavily in relief, her knees shaking. “Happy to hear it.”

“This discussion ain’t over.”

“The hell it is.”

She felt his chest rumble in mild laughter. “But you ain’t gettin’ rid of me.”

“Thank God.”


	19. Chapter 17

They didn’t really talk anymore that morning. Instead, they both curled up on the lumpy mattress that was Y/N’s incredibly shitty bed. Dean complained for quite some time about the fact that it was the “worst thing he’d ever slept on,” but, eventually, they got a few hours of sleep before work.

When they woke up a few hours later, Dean had made a decision. He declared that she absolutely could not stay there any longer.

“Dean, I’ll be fine. I’ve been fine so far.”

“With that mattress, I can’t believe that.”

She chuckled at that. “I’m gonna hear about that mattress forever, aren’t I?”

“No, you’re not, because you’ve never sleeping on _that_ again,” he shuddered. “Pack your things, you’re movin’ in with me.”

Red fell over her entire face and, suddenly, the room was too hot to live. “Dean, I can–”

“Yes, yes you can. My place is safer and you _know_ it’s more comfortable than this bologna!” he looked at the bed like it was the most disgusting thing he’d ever seen.

She shrugged. “This room is fine. I’m not here often enough for it to matter.”

“Y/N,” he placed his hands on her shoulders, forcing her to face him. “You love me.”

She blushed slightly more. “Yes.”

“And you are working with Bobby and lied to me about it.”

She slouched a little, frowning. “Yes.”

“So you love me _and_ you owe me.”

And that’s how she ended up checking out of her crap motel and into Hotel Winchester.

* * *

That night, Y/N watched as Dean smacked Gabriel Novak on the shoulder. Gabe looked really confused, his hazel eyes narrowing as Dean gave him a tight smile and before he walked away.

Her answer to the drummer’s confused look was a simple, “He thought you and I were doing something we shouldn’t’ve been.”

Gabe smiled, still a little concerned. “Well, that’s your department, doll. He know?”

“Yeah.”

The drummer looked shocked at that. “Wow, you actually told him.”

“Technically,” she began, looking away in embarrassment. “He might’ve found me out.”

“And…and you two are okay?”

She smiled softly. “Yeah. I mean, it’s still…an issue. But I think we’ll be okay.”

He wrapped an arm around her shoulder and pulled her into a hug. “You better. I’m rootin’ for you, kiddo.”

Her own arm wrapped around his waist, and she smiled brightly at him. “And you say you’re a selfish schmuck.”

“I am, and don’t you let anything convince you otherwise.”

She laughed, disentangling herself from the drummer and heading into the back room to join her boyfriend. “You’re doin’ that all fine by yourself.”

Gabe scowled. “You shut your cake hole!”

* * *

The night ended splendidly. It was like before, with Dean pulling Y/N into a corner every chance he could to pepper her with kisses and finding any chance he could to touch her. During their performance, she’d practically felt his eyes boring into the back of her skull. _That_ had caused her temperature to rise for a reason having nothing to do with the burning hot spotlight that clung to her like a second skin.

Gabe and Meg had teamed up to made snide comments about the changed atmosphere all night. Just when the couple had escaped one of their tormentors, they’d be flanked by the other. Thus, the lewd jokes continued all throughout the night.

At one point, Castiel had even left the bar to bring Meg away, claiming to need her assistance. He’d shot the couple a sympathetic look, and Y/N could’ve kissed him.

However, other than those few things, the night ended without incident.

The entire crew sat around for a moment, enjoying the renewed cheer. No alcohol was served (something Chuck and Gabe were sure to mention often), but everyone was a bit drunk on the sudden influx of joy back into Crowley’s.

One by one each member left as the night wore on. They all made sure to go over to Dean and Y/N and give them each a tight hug. She’d caught Castiel telling Dean how happy he was that the two had “resolved their differences,” a sentence that made her hug Cas so tight, Meg had to pry Y/N away before the bartender passed out.

Finally, it was time for Dean and Y/N to head out.

To head home.

To Dean’s apartment.

She took Dean’s free hand as they drove back to his– _their_ apartment. What a weird thought. She’d never really had a home, not since the orphanage, if that even counted.

And here was Dean, being much better than anything she deserved, giving her his home and his heart.

She watched him as he drove. His hunter green eyes focused on the road, the street lamps bringing out the constellation of freckles that littered his face. Her eyes trailed down his strong jaw, his straight nose, the column of his thick neck–

And that train of thought needed to stop right this moment.

But did it?

She scooted over and across the bench seat, curling up into Dean’s side. He seemed surprised, but quickly wrapped an arm around her shoulders, pulling her even closer.

Quiet reigned a little bit longer before she spoke. “Do you know the first day I met with Agent Singer?”

He frowned. “No. Can’t believe you brought it up either.”

She nuzzled into his shoulder. “Bear with me, Dean.”

She felt him shrug slightly, signalling silently for her to continue.

After a deep breath, that’s what she did. “The first day I met with Bobby, it was the day after…after the last night I spent in your apartment.”

“Okay,” He nodded, looking a little confused still. “Why bring this up?”

“That’s why I was acting so weird that day,” she confessed, watching him closely.

“Oooookay…”

She huffed. “Not because-a you. Or anything you did.”

The car slowed to a stop in front of Dean’s building, and he waited until the car was taken care of before turning to her. “So, I didn’t…I didn’t push you too far?”

Her sigh was one of a mixture of relief and irritation. “No, Dean. I was…I wanted to, so badly.”

Hope sparked in him at that. “YOu…you did?”

She smiled brightly, a soft pink darkening her cheeks. “Yeah…st-still do, honestly.”

“Wait,” a gigantic grin spread across his face slowly. “You do?”

She nodded. “I love you, Dean. I have for a while now, and I…I want to.”

His emerald eyes stared deep into her Y/E/C eyes, looking for any indication that she might be lying or was unsure. When he found no hint, he nodded slowly, like he was still processing the information. “Okay, you…that’s…”

She squeezed his hand. “We could…maybe tonight?”

He frowned. “I don’t want you to feel like you haveta.”

In a sudden spurt of confidence, she frowned and said, “Dean, how can I convince you to take me upstairs and ravish me?”

His eyes widened and, had he been drinking something, he probably would’ve spit it out in shock. Then that shock morphed into a big smile, the smile of a kid getting the best Christmas present he could ever ask for.

He hopped out of the car without a word, running around to open her door.

She looked up at him, confused, when her door opened and he held out his hand.

He laughed, “Well, c’mon doll! I can take a hint.”


	20. Chapter 18

**Notes for the Chapter:**

> Hey, so this chapter is 100% smut. That's it. No story, no nothing. Plot will resume next week. This is just a warning to those who don't like smut that you are okay skipping this chapter.

“I’ll be right back, I promise.”

“I know, Dean, I’ll be here.”

They had barely made it inside the apartment before Dean had realized that they were unprepared for their planned activities. So, he had made the adult decision to run down to the nearest open liquor store and acquire what they needed.

So, he had peeled himself off of her from where they had landed, tangled together on his couch. Now, he stood above her, panting heavily, and staring down at her with lust-blown pupils.

“So, don’t move, alright?”

“I’m not going anywhere,” she smiled softly.

“And I’ll be really quick, so just, y’know, make yourself comfortable, and you can help yourself to any—”

“Dean, _go_.”

“Yes, ma’am!”

With that, he was out the door with one last, searing kiss.

She fell back against the couch, sighing heavily. She bit her lip to contain the high-pitched squeal that wanted to leave her at that moment.

She sat up, absent-mindedly fixing her outfit and making herself a little more presentable. Then she thought about it, and she felt more than a little stupid.

She got to her feet and began walking over to the bedroom. She stood in the doorway, staring at the bed, her heart still pounding.

Before she could think twice about it, she ran back out to the couch and threw her coat over it.

Then she stepped a little closer to the bedroom and kicked off her loafers.

Then a little closer, she shed her stockings.

A little closer, and there went her skirt.

Right in front of the bedroom, she got down and laid out her shirt in what she hoped was an enticing way.

Now in just her underwear, she surveyed her handiwork. Satisfied that it was acceptable, she turned to the bed. Quickly tucking in the sheets, she made it look nice and presentable before climbing on top of it.

She sat awkwardly in the middle of the bed for a moment, trying to decide how best to approach the situation. She laid back against the pillows, crooking one knee and letting the other rest flat against the mattress—Dean’s mattress really was a hundred times better than her shitty motel one—and took a deep, steadying breath. She let her arms rest atop the pillows on either side of her and tried to settle in.

No, this was _entirely_ wrong.

She crawled onto her hands and knees before lying down on her stomach. She rested her elbows in front of her and her head in her hands as she kicked her feet up behind her.

No, this was worse.

She rolled over onto her back, sprawling out. She huffed, frowning.

Maybe it was her outfit, she decided. She could dig through her bag of things that they’d brought from her motel room, see if there was anything better.

Who was she kidding? She didn’t have anything nice for this kind of thing. She was an idiot—Meg had been teasing her for almost as long as she’d known her, offering to take her to the department store lingerie section, “get a present for Dean,” and she’d been too embarrassed to take her up on it.

So there she lay on his bed in her comfortable but wholly unsexy underwear.

She glared at the ceiling, wracking her brain for her next move. Crawling back up the bed, she planned to lie on her side facing the doorway when she heard the front door burst open.

There was a moment of silence, and she took the opportunity to throw herself against the pillows again. She heard Dean’s gruff voice mutter something that sounded a lot like “son of a bitch” as she tried to remember how her limbs worked.

The door of the bedroom opened slowly, the hinges creaking quietly.

Y/N was sprawled out awkwardly on the bed in her increasingly unattractive underwear. She stared up at Dean, feeling more than a bit like a deer in headlights.

He looked a little out of breath—had he run to the store and back?—as he leaned just slightly against the doorjamb.

Her brow furrowed and she crawled up to rest on her knees. “Are you okay, Dean?”

“I’m perfect, doll,” he pulled out that stupid grin, the one that always made her heart flutter like a damsel in a romance novel.

His eyes roamed over her, the grin turning into a soft smile. His emerald eyes met her Y/E/C ones, and he seemed unsure of himself for a moment. It was so strange to see that concern cross his face and she wanted nothing more than to take it away. “You sure, sweetheart?”

She huffed out a humorless laugh. “I, uh…really?”

The hand that wasn’t holding the small brown paper bag went up to rub the back of his neck. “I just…you deserve better.”

She crawled off the bed, walking up to stand toe to toe with Dean. “Pretty sure you got it backwards, Dean.”

He frowned and said nothing.

She took the bag from his hands and tossed it onto the bed. She then removed his hand from the back of his  neck, twining their fingers together. She leaned up into him, standing on her tip-toes, and pressed a kiss to his lips.

He let go of her hands, one immediately going into her hair and the other to the small of her back, resting on the silk of her shorts. Her own hands wrapped around his neck, holding him to her.

When she pulled away, she took his hands once more, pulling him towards the bed.

He laughed as she sat down, still tugging on him. “Doll, I think I’m more nervous than you are.”

She smiled. “I’m just hiding it better. Gimme a minute.”

Dean crawled atop her, his lips fastening to hers once more. She opened her mouth for him almost immediately, pulling a quiet groan from him.

His hand found a home on her waist, his pinky playing with the elastic of her slip. She arched into him, trying to silently communicate with him. He seemed to understand, though, since he began pushing down. He shoved it all the way down and she kicked it off once it was low enough.

Her own hands went to work, trying to undo his vest with shaky fingers. He shucked off his coat before helping her finish off his vest, which joined his coat on the floor. She immediately began unbuttoning his shirt whilst he went for his pants.

He got his pants undone before she finished with his shirt and he finally moved away from her, sitting up on his haunches. She grinned, following him up. She let her lips fall to his neck, kissing on the tender skin under his jaw as she fumbled with his shirt. He pushed her back a little to get his tie, then leaned down to intercept her lips once more.

Smiles were plastered on their faces, tiny giggles the only thing to be heard in the quiet, dark bedroom. Finally, his shirt was unbuttoned and it nearly came off, before getting caught at his wrists.

She snorted trying to keep her laugh in. He was obviously a little embarrassed, a little flustered, but a lot laughing with her. He undid the buttons on his wrists as Y/N’s hand ran up to trace the bit of tattoo under his collar bone that poked out through his undershirt. She leaned forward, kissing it through the fabric.

When she pulled away, he was staring down at her with a warm, loving look in his hunter green eyes. She answered with a giant smile. “I love you, Dean.”

He answered her by ripping off his undershirt before introducing their lips again. She wrapped her arms around him, her soft fingers exploring the huge expanse of his back. Her tongue rolled across the seam of his lips, and he was happy to oblige. Their tongues danced for a few moments before she pulled back. “Pants.”

He smiled widely, leaning down to peck her on the lips once more before flipping around to sit on the edge of the bed and begin ripping his shoes, socks, and pants off. As he worked, she wrapped her arms around his shoulders from behind, kissing along his hairline and the shell of his ear.

“Sweetheart,” he said breathlessly. “I can’t concentrate on this when you’re doing that.”

She hummed in response, but didn’t stop.

“You’re gonna kill me.”

She chuckled, her fingers dancing down his chest.

That seemed to spur him on more. She squeaked as he suddenly flipped around, clad only in his boxers, and pinned her down to the mattress. The kiss pressed against her lips was bruising, but quickly over in favor of trailing down. His plush lips traveled down over her collarbone, marking his territory with little bites. When he reached her bra, he kissed along the edge of each cup, making Y/N whine and writhe beneath him.

His right hand trailed feather-light up her spine, her back arching to give him room. He finally reached the clasp at the back and unsnapped it with ease.

She was shrugging off the straps before he could react. His slack-jawed expression as she threw the undergarment to the side was priceless.

“God, sweetheart,” he almost growled, leaning down to attach himself to one of her nipples.

She gasped, suddenly forgetting how to breathe. His hand acquainted itself with her free breast, and her fingers with Dean’s short hair. His teeth grazed her nipple and she nearly tore out entire chunks of his hair. He switched, quickly kissing his way over, and she wrapped her legs around his hips in response. “Dean,” she begged.

He pulled back, leaning up to kiss her again. Her hands left his head, trailing down his chest to his boxers. Her fingers played with the edge of his boxers. When he thrust his hips against her hands, the hard length hidden underneath the fabric hitting her right in the crux of her thighs, she took the hint.

Her hands reached around, pushing down the boxers enough to grab two handfuls of his ass. She gave a squeeze, which made Dean laugh. “Think I know what you like, baby doll.”

“One of many things,” she wiggled her eyebrows playfully.

Then she pushed his boxers down enough for him to shimmy the rest of the way out of them. She pulled back, desperate for a look. His cock was standing straight, the head of it red and with a small amount of precum leaking.

She froze up a little at the size of it, which Dean noticed immediately. “You okay, doll?”

She nodded, her Y/E/C eyes not moving.

He sighed and cupped her cheek, forcing her to lock eyes with him. “Hey,” he whispered. “We can stop right here, right now.”

The tension immediately left her, and she leaned up to press a soft, sweet kiss to his lips. “I don’t want to.”

He pulled back. “You’re sure?”

She nodded. “Yeah, I just…I wasn’t expecting it to…” she flushed, her entire face turning bright red.

A big, Grinch-esque smile crossed his face. “Oh? Really? _What_ weren’t you expecting?”

“Shut your face, Winchester.”

“Well, I’m just curious,” he leaned down, his lips ghosting against her ear. “What weren’t you expecting?”

“You know damn well, Dean,” she grumbled.

“Hmm, can’t say I do.”

“I’m not saying it. Your ego’s big enough.”

“My _ego_ , you say?”

Her hands covered her face and she groaned out loud. “Why do I love you again?”

“I’m adorable.”

She laughed, her hands falling away. “That must be it.”

He nuzzled into her neck, turning her quiet laugh into full-blown giggles. Then his hand trailed down from her ribcage to her panties, and the giggles stopped.

Her hand reached down, experimentally touching his dick. He groaned like he was in pain before pulling back.

She frowned, sitting up on her elbows. “Are you okay?”

“Maybe a little too okay,” he laughed without humor. He took a deep, shuddery breath before he spoke again, “I just…it’s been a while for me, and I don’t wanna end the night early.”

She nodded slowly. “O…Okay…”

He pressed a quick kiss to her lips. “Next time, I’m gonna be begging you to do that, though.”

She smirked. “I won’t make you beg.”

He groaned. “Focus, Dean,” he mumbled to himself.

Without another word, he tore her panties down her legs, making her yelp. Then he was rubbing his middle finger through her folds, which made her shout in surprise. He grinned, and she lightly slapped his chest in recompense.

He leaned down, kissing her deeply as his finger rubbed her slick over her lower lips. The moment he found her clit, she dug her nails into his bicep, trying to keep quiet. “Fuck me, Dean,” she moaned, her head falling back against the pillow.

The smirk he gave her was almost audible. “That’s the plan, sweetheart,” he spoke quietly, pride lacing his tone.

“You’re insufferable,” she ground out, trying to form words and not moans.

“I love you too, doll,” he answered, almost nonchalantly.

Tears built behind her eyes, but she laughed quietly in disbelief. “Well, how could you not?”

He leaned down, kissing her soft and slow, his left hand resting between her shoulderblades as his right hand went back to work at her clit.

She moaned against his mouth as her hands flew to the warm expanse of his back, feeling the muscles work deliciously under her fingers.

Then, one finger teased her opening. She pulled away from the kiss, resting her forehead against Dean’s. His hot breath fanned over her face, somehow making it even harder for her to breathe.

When his finger slipped inside, she completely forgot her own name.

“Doll, you gotta relax,” Dean cooed, peppering her face with kisses. “I don’t wanna hurt you.”

She whined quietly, tilting her hips up so he had better access.

His smile could be felt through the kisses along her jaw. He pumped his middle finger in and out of her slowly, working her open as gently as he could.

What felt like a thousand years later, his pointer finger joined in. Now with a partner, his fingers got a little more daring. They scissored and crooked, trying to find every spot in her that made her squirm and cry out for more.

Finally, he slid a third finger in her and she grabbed his face, pulling him in for a kiss. “Dean,” she panted. “ _Please_.”

A low string of obscenities left his bruised lips. He got off of her, reaching down to the floor where the bag he had brought home lay. He reached in and pulled out the small box of condoms he’d bought, ripping it open quickly. He used his teeth to remove the next bit of packaging, revealing his prize. With a speed she’d not seen from him before, he rolled the condom down over his length.

Dean then laid down on his back, holding his hand out to Y/N. She took it, eyeing him strangely. He lightly tugged her closer via their connected hands. “Put one leg on either side of me, sweetheart,” he whispered. She did as requested, awkwardly settling in. Once she seemed comfortable, he pulled her down to his level, kissing her once again, holding her as close as humanly possible. She clung to him, finding even one centimeter of space between them unfathomable.

She pulled away, sitting up on top of Dean and breathing heavily. Her face flushed at the position and she stuttered out, “Um…shouldn’t you—?”

“You can control how fast we go this way,” he answered quietly, his hands running from her waist to her rib cage. As they wrapped around to find purchase on her shoulder blades, he sat up, pulling her into a sweet kiss.

Her own hands cupped his cheeks, holding his face to hers. “And you say _I_ deserve better.”

He chuckled. “Agree to disagree?”

She kissed him once more, a quick, close-mouthed kiss, as she felt his hand slide down her back to where their hips were resting near each other. She sat up a little more on her knees, giving him room to maneuver his hand in between them. He gripped the base of his cock, rubbing his tip along her folds. Her head fell into the crook of his neck, biting her lip to hold in the moan that threatened to leave her.

She felt her hair being pushed away from her face a little. “You ready, doll?”

She nodded, wrapping her arms around his shoulders. She mumbled a profession of love against his skin as he finished lining himself up with her entrance.

A small kiss was placed to her temple, and his free hand rubbed soothing circles into her back. “Whenever you’re ready, sweetheart,” he spoke, his voice slightly strained.

Not wanting to make him wait any longer, she began sinking down.

The hand that had been holding him in place flew up to grip her hip tightly. She could already feel the bruises forming.

It burned a little, but not as much as she had worried. She had to stop once to take deep, shuddering breaths. Dean held her close the entire time, whispering how perfect, how beautiful, how amazing she was into her ear.

When she was finally rested against her hips against his, it didn’t hurt too much. She pulled herself from the crook of his neck and looked down at Dean.

He smiled up at her. “You’re doing so good, baby,” he whispered.

She huffed out a laugh, holding him tightly against her. “Sorry, I need a moment.”

He brought her head down, “Take your time,” he mumbled against her lips. “We got all the time in the world.”

Y/N sat up, took a deep breath, and rolled her hips. It stung a little, but the look on Dean’s face made her forget all about that. She rocked her hips back and forth, clutching to him tightly as the pain gave way to pleasure.

The hand on her hip guided her gently, whilst the hand he had on her shoulder blades pushed her up against him, smashing their chests together.

She sped up bit by bit, the band in her stomach tightening with every move of her hips. Soon enough, she was moaning out Dean’s name and broken expletives into the ether.

That broke him.

Without warning, she was flipped onto her back, Dean holding himself up by his elbows above her, a smirk on his face.

She grinned brightly leaning up to kiss him as he pulled out and pushed into her.

The new angle let Dean hit a spot inside of her that she had never been able to reach herself. She keened, scratching at him like she was blind and searching for purchase.

One arm wrapped around her waist, the other holding himself up as he began pounding into her.

The sounds leaving Y/N’s mouth could, in the broadest sense of the word, be counted as sentences. Usually punctuated with a curse word rather than a period, she began praising Dean, telling him how much she loved him.

He responded by whispering how beautiful, how tight and hot and wet she was, and how he wasn’t going to last long.

He sat up on his haunches, pulling her onto his lap. Now not needing to hold him up, his hand found her clit and began rubbing at it harshly.

She gripped tightly to the sheets by her head. “Dean, I’m gonna—”

“I know, c’mon, doll,” he whispered hoarsely. “Come for me.”

The sound that left her mouth was not one either had ever heard leave a human before. A half dozen more thrusts, working in tandem with his calloused fingers working the tiny bundle of nerves where they were connected, and she fell over the precipice.

His name left her lips in a strangled prayer, and she vaguely felt him pump into a few more times before her convulsions sent him spiralling into his own orgasm.

Dean fell forward, catching himself on him hands and hovering above her.

Y/N laughed breathlessly, grinning up at her lover. Her hands grabbed him by the neck and pulled him into a sloppy kiss. He pulled back and began peppering her face with kisses, causing her to giggle even more.

When they began to cool, Dean stopped his kisses and pulled his softening cock out of her (which was probably the strangest feeling of the night for her) and disposed of the condom. He walked out into the bathroom, and she heard the tap running for a moment before he returned, a ratty-looking washcloth in his hand. He rubbed soothing circles into her hips and waist as he cleaned her up. Once he cleaned himself up, he threw the cloth into a pile of laundry. She’d taken the chance to pull back the covers and snuggle up under them whilst he was busy. When he turned back to her, she held the blanket up and patted the mattress with her free hand.

He made himself comfortable under the blankets, laying on his back and letting his girl use his arm as her pillow. She rested her head against his tattoo, her fingers tracing random patterns into the far side of his ribs.

She looked up at him, resting her chin on his chest. “I love you, Dean.”

He smiled down at her, pressing his lips to her forehead.

“Thank you. For… _this_ , for letting me stay here, for—”

“Doll, I love you, but you’ve tired me out. Can we have girl talk in the morning?”

She smacked his chest hard enough for the sensation to be just shy of painful. “Oh, you’re so lucky I’m tired too, wise guy.”

He laughed, pulling her closer. “I’m lucky for a lot-a reasons, sweetheart.”


	21. Chapter 19

The next morning came much too soon.

Y/N awoke to the feeling of fingers running up and down her spine. She smiled and snuggled closer into her lover. “G’mornin,” she mumbled against his chest, not yet opening to her eyes.

“Good morning,” he said, leaning down to press a kiss to the top of her head.

“Gotta say, Winchester,” she tightened her grip around him. “This is a nice way to wake up.”

“Agreed,” he chuckled.

They lay there for a few moments more before the growling from Dean’s stomach became unbearable.

Y/N tried to pull away, but Dean refused to let her go. He rolled them over, leaning over her and attaching his lips to her neck. She went between giggling and moaning Dean’s name.

Then her hands trailed down his sides, and he barked out a laugh.

The couple stared at each other with wide eyes. Then Dean’s emerald ones narrowed in what was supposed to be a threatening manner.

Y/N pursed her lips, her shoulders shaking as she tried to hold in her laugh.

“Not a word, Y/L/N.”

Her shoulders shook harder.

“Y/N…”

“You’re…you’re ticklish?”

“Shut your mouth, Y/N,” he growled.

She threw her arms around his shoulder, burying her face into the junction of his neck as her stifled laughter began to leave her.

Dean sighed dramatically. “Fine, see if I make you breakfast now,” he grumbled.

She let go enough to let herself fall back onto the mattress. “I swear, Dean, that I will only use this to my advantage when we’re at home.”

He groaned flopping onto his back. “I’m never gonna live this down.”

“Nope,” Y/N licked her lips, bringing her bottom lip between her teeth as her tongue retreated. She then took a deep breath and straddled her lover, letting the blanket fall away and exposing herself completely.

His pupils dilated even as a look of shock came over him.

She smiled coquettishly (she hoped), and leaned down, brushing her lips against Dean’s. “But maybe I can make it up to you…?”

She squeaked as she was suddenly flipped over and given a wonderful repeat performance from the previous night.

* * *

Y/N and Dean had settled in rather nicely to their new life together. They went into the club each day (when she had walked in on wobbly legs the day after their first night together, Gabe ended up getting his fin back from Benny), performed, and went home.

Dean refused to leave her side the entire time.

At first, she thought it was because he was constantly stealing kisses and tracing her fingers over any bit of exposed skin he found. Ever since they’d made love, he was a lot more tactile, looking for any excuse to touch her.

Then she thought harder on it.

He would wait for her in the hallway when she changed, not in the bar with Benny and Cas. He wouldn’t let her alone for even a second. As much as she loved him, she was desperate for some breathing room.

She didn’t think that it was because of the sex, though. That was definitely a thing they were exploring, which was definitely not a problem for her.

However, she noticed that he seemed to position himself to block her view of anything that could help Agent Singer.

He’d stand with his back to Crowley’s office, distracting the singer with kisses and whispers into her ear of what he planned to do with her once they returned home for the evening.

She wasn’t stupid, however, and she knew his game.

Which is why she wasn’t surprised when Friday morning rolled around, and Dean was insisting he join her for their meeting.

“What do you think will happen, Dean?” she huffed, sitting in the bed, holding the blanket to her chest.

The pianist had just slipped into his pants, buttoning them up and refusing to make eye contact with her. “Nothin’ with me around.”

She groaned, rolling her eyes. “Dean, I’ll be fine. You should stay home, get some rest for tonight.”

“Can’t do, sweetheart,” he gave a strained smile before pulling on his undershirt.

She huffed, crossing her arms.

He sighed, walking over to the bed to sit next to her. He pried one of her hands from her, taking it and lacing their fingers together. “C’mon, doll,” he whispered against her knuckles. “Please don’t leave me here. I’ll go crazy.”

She glared at him. “Fine. But you don’t…don’t start nothin’, you got me?”

He nodded, leaning forward to press a soft kiss to her lips. “Thanks baby.”

“You’re lucky I love you,” she mumbled.

He smiled softly. He let her hand go and grabbed a dress from the closet. “C’mon, I’m starving!”

* * *

The Roadhouse had, in a lot of ways, become a safe haven for Y/N over the few weeks that she’d been helping Agent Singer.

So, she was nervous. She knew that Dean knew everyone inside already, but hadn’t spoken to them in some time, probably since he began at Crowley’s. What if it was awkward? What if she was intruding? What if they decided that she wasn’t good enough for him?

It was official: nothing good could come of this.

Dean had his arm wrapped around her shoulder, holding her close and trying to protect her from the biting early morning wind. He pushed open the door to the diner with his free hand.

The bell rang, signaling their arrival to the seemingly empty restaurant.

Dean offered to take her coat. Y/N shrugged it off her shoulders and he took it from her after removing his own coat. With both wrapped over his arm, he took her hand in his and began moving to a booth near the door.

She didn’t move, which caused him to look back confused. “We got a regular spot,” she explained, pulling him towards the back.

He followed, not saying a word. She scooted into the booth, with Dean sliding in beside her. His arm rested on the back of the booth, almost like it was back around her shoulders. She instinctively cuddled into his side some more, hating an even inch between them.

A few more moments passed before Jo walked up, looking down. “Hey, Y/N, sorry, we got in a lil’ later than–” she stopped short once she looked at her friend and instead saw the pianist. “D-Dean?!”

He smiled awkwardly. “Hey Jo.”

She huffed out a laugh. “That’s all you got? Where the hell ya been?”

He shrugged. “‘s complicated.”

“Bullshit.”

Y/N snorted at that, reminding the blonde that she was there. “Oh… _oh_.”

Dean frowned. “What?” he asked defensively.

“Nothin’, just…are y’all…” she motioned between the two of them. “Y’know?”

The singer nodded. “Um, yeah, actually.”

Jo revealed a big grin. “That’s swell!” she then turned to him, her chocolate eyes narrowing and the smile falling from her face. “Dean, you better be treatin’ her right!”

Y/N laughed at that. “He’s been wonderful.”

“He better be! He knows what’ll happen if he screws this up,” she needled.

Dean gulped, looking scared as hell. Y/N’s head cocked to the side. “What, Dean, ya scared of Jo?” she teased.

He shook his head. “Jo? No. Her mom? Hell yes.”

The girls laughed at that. Jo then took Dean’s order, already knowing Y/N’s, and headed back. She promised to send everyone by to say hello, and that only seemed to mortify him more.

Maybe this wasn’t so bad.

Ellen had come out a few minutes later with the biggest grin she’d ever seen on the older woman. She stood there, threatening to not move until she got a hug from the Winchester. He’d reluctantly agreed and Y/N wished for nothing more than a picture of the moment. His embarrassed and slightly guilty expression was priceless.

Ellen had reiterated her daughter’s threat, silently promising terrible things to him if he broke Y/N’s heart.

“Glad to know where your priorities lie,” Dean had grumbled.

When he’d plopped back down in his seat, Y/N had pulled him into a kiss.

He smiled into it, calming a bit.

When she pulled away, he cupped her cheek, rubbing his thumb along her cheekbone. “They’re never gonna make good on their threat.”

“Why, do they often make threats they don’t keep?”

“No, ‘cause I ain’t stupid enough to let you go.”

Her face turned beet red at that, and she bit her bottom lip as she beamed. She looked down, picking up his other hand and playing with his fingers. “Good.”

With that, their lips met again, Dean’s hand moving from her cheek to the base of her skull, holding her close.

Then the bell over the door jingled.

They pulled away, both turning towards the door.

In strutted federal agent Robert Singer. He was yawning, his eyes closed and mouth open. He was halfway out of his coat before he noticed the new addition to the table.

“Hey Bobby,” Dean gave a tight smile.

Agent Singer sighed heavily. “Balls.”


	22. Chapter 20

**Notes for the Chapter:**

> So, I just…I’ve been having a bad few days, and this nearly didn’t get out. That’s why it’s so short, and I sincerely apologize. I have no real excuse. Fun times :D

Agent Singer and Dean had been arguing for about five minutes by this point. Y/N had moved to the diner’s bar, where Jo had been kind enough to serve her. Ash, who had finally come out to say hello to his friend, had immediately retreated to the kitchen.

Jo leaned over the counter, her eyes moving back and forth between the singer eating silently and the argument in the corner. “Haven’t they tired themselves out yet?”

Y/N shrugged. “I think they’ll stop when they run outta air.”

Jo laughed. “Give it a minute more, and my mom will come out and shut them up.”

Y/N shuddered. “Maybe we should warn them.”

“You kiddin’?” Jo grinned evilly. “And miss the show?”

The girls giggled quietly to themselves, eagerly awaiting the smackdown.

Ellen did come out a few minutes later, and Jo would later describe what happened next as “so good, she felt like she should’ve bought a ticket.”

Within moments of Ellen entering, both men were seated back in the booth, looking like two kicked puppies.

Y/N, now finished with her small breakfast, slid in beside Dean, linking their fingers together as soon as they were close enough. He squeezed her hand, even giving her an awkward smile.

“I thought I told you—” Agent Singer started gruffly. Jo cleared her throat at the bar, which made the federal agent stop speaking. He took a deep breath and, with once more began speaking, though this time, with a softer tone. “I thought we _discussed_ you not tellin’ Dean.”

“She didn’t,” Dean grumbled. “I ain’t stupid, Bobby.”

The older man’s eyes narrowed. “Well, now you know, then. I’m guessin’ you want this to be our last meeting.”

Y/N spoke again. “No, it’s not.”

At the same time, Dean had answered. “I wish.”

The look on the agent’s face was priceless. “What?”

Y/N rolled her eyes. “I’m not stopping. I’m going to help you, Agent Singer.”

Dean’s frustration was rolling off of him in waves, and, in his corner of the booth, he began pouting a little, though he’d never admit it.

Agent Singer\s brown eyes switched back and forth between the couple, a mixture of confusion and amusement showing on his face. “So, why is Dean here?”

“He isn’t taking the news well, that’s all,” she answered.

Dean grumbled, running a hand down his face.. “Look, Bobby, no offense, the last time you showed up at the club it was a _gas_ and all, but I’d appreciate not sitting through a repeat performance.”

That made the older man noticeably uncomfortable. He apologized quietly, sincerity dripping from his words.

Dean shook his head. “I didn’t…I just need you to understand why I’m—”

“I’ve always understood, boy,” Bobby interrupted.

Dean licked his lips as he searched for the right words.

Y/N squeezed his hand. “Bob—Agent Singer,” she began. “Dean just wants to make sure I’ll be safe. That’s all. He’s not helpin’ or hurtin’ us.”

Bobby sighed heavily. “I wish you’d help us, boy.”

“Bobby, I’m already doin’ more than I ever wanted to. This is too much. You want my help, you put a detail on Sammy,” Dean chuckled.

Bobby sat back in his seat. “Really?”

“What?”

“Is that all it takes?”

“Bobby, no—”

“Well,” Y/N interrupted. “You _did_ say—”

“I was joking, sweetheart.”

“It’d be nice to see the kid. He’s gettin’ married soon, isn’t he?” Bobby turned to the singer, obviously amused.

“So everyone says,” she smiled.

Dean leaned forward on the table, resting on his elbow. “No, both of you—”

“”You _are_ the one that offered, Dean,” she cut him off. “And if you’re gonna insist on comin’ here and havin’ breakfast with us each week,you should at least give Agent Sin—excuse me, _Bobby_ —a reason to pay for your food. It’s really the polite thing to do.”

“Your girl knows what she’s talkin’ ‘bout,” Bobby added. “Don’t screw this,” he motioned between the couple. “Up.”

“Ellen already gave him the talk.”

“Shit, _Ellen_? You know you don’t wanna get on her bad side, boy.”

“Enough!” Dean’s face was beet red, in embarrassment or frustration, they weren’t sure.

There was a tense moment of silence before the pianist spoke again. “Y/N’s already involved.”

“Neck deep,” she clarified.

His jade eyes narrowed at her, but he continued without comment. “What was her price?”

“I resent the accusation that he bought me,” she frowned, her fingers moving lightly along his side in a silent threat.

She saw him bite back his laughter, but it was subtle enough that, perhaps, Agent SInger hadn’t noticed it.

The smirk on Bobby’s lips told her that he had. But, he answered, “She wanted me to keep you safe.”

Dean blinked at that. “Wait…what?”

“That’s all she asked for, Dean,” he rolled his eyes. “What part of ‘don’t screw this up’ are you not gettin;?”

Dean’s hand squeezed hers, and she knew that the two would have to discuss this further later. “So…even if I don’t help…it’ll still look like I am if Crowley ever finds us.”

The silence returned.

Dean continued, “So…if you _swear_ to me that Sam’ll be safe.”

Bobby sighed heavily. “I can tell you that I’ll have some California morons watchin’ him.”

“Well, that’s reassuring.”

“Unless you wanna bring him out here so I can keep a close eye on him—”

“ _No_.”

“Then that’s what I can offer.”

Dean ran his hand down his face again, sighing heavily. His shoulders were slumped like he was carrying a huge weight. Y/N’s free hand went to his upper arm, rubbing his bicep soothingly. His hand squeezed hers again.

“Fine,” Dean spoke without looking up from the tabletop. “I’ll…I’ll help.”


	23. Chapter 21

**Notes for the Chapter:**

> And thus the prodigal series returns! With…backstory. Wow. Exciting. :D

The rest of the meeting went smoothly. Dean was tense the entire time and frequently ran his thumb along Y/N's knuckles to try and calm himself.

When the meeting was over, Agent Singer pulled Dean in for a tight hug, then backed away awkwardly.

Dean had nodded, pursing his lips before turning on his heel and walking out of the Roadhouse.

Y/N said goodbye on his behalf, then ran out to join her pianist.

They didn't speak on the drive home. He ran his hand down over his face once or twice, but that was the extent of his communication.

In fact, no words were exchanged until they were back in their apartment and the door was closed and locked behind them.

Y/N was halfway out of her coat when Dean grabbed her by the shoulders and pulled her into a bruising kiss.

She was a little dazed, but she finally mumbled out a "Wuh…what was that for?"

"Thank you," he mumbled after a beat of silence.

She frowned, but laughed it off. "Well, whatever I did, you're welcome."

Dean's hands moved up to cup her cheeks, his thumbs running along her cheekbones. He stared at her a moment more before pressing a soft kiss to her lips.

She hummed in contentment, then covered his hands with her own. "C'mon, let's get some more sleep," she began pulling him back into the bedroom. "Maybe I'll remember what I did when we wake up."

He chuckled lightly, but said no more.

* * *

Unfortunately, the weekly meeting between Y/N and Agent Singer had been rather highjacked by its unexpected addition to the party; ergo, she wasn't sure how the investigation was going on his end.

On the way into work that night, she spoke with Dean, explained to him how Gabriel had caught her and she's caught the name of Crowley's bank and Bobby was looking into that.

He, in turn, finally told her how he met Bobby, saying that there was "no point in hiding it anymore."

"My mom died when I was four," Dean began. He tried to state it as a fact, but his face betrayed him: he still felt her death as freshly this day as he did twenty-three years earlier. "In that big outbreak in 1918. Dad couldn't…he needed someone to blame, y'know? So he'd be out, trying to find answers either at the hospital or at the bottom of a bottle. Sammy…he was just a kid, y'know? Not even a year old. And I _had_ to take care of him. It was my job, the one thing my Dad drilled into me: 'look out for Sammy.'"

Dean's voice was even, even enough to worry her. She slid across the bench seat, curling into his side and hugging him close, trying to give him an emotional heimlich and get him to spit up whatever turmoil was in him.

He wrapped an arm around her shoulders, squeezing her. Then he continued, "Anyway, one day, Dad met Bobby at the hospital. Bobby's wife she…she died too a couple-a years later. After that, and after Dad found out that Bobby was a copper, he would leave us at Bobby's all the time when he got too drunk.

"But, still, Bobby he…he didn't want these two stupid kids at his place all the time. He and my dad they fell out, but Bobby never kicked us out. He'd take us to the park and made sure we got to school and…he raised us. He raised me an' Sammy more than our dad ever did. Hell, I haven't spoken to my dad in _years_ , but Bobby…"

Y/N let her head fall onto his shoulder. "Is he the one who taught you how to work on cars?"

Dean grunted in agreement. "The car is from my dad, though. Jus' easier to tell people that it's all the same person than 'oh this guy who's a better dad than my actual dad taught me to fix up the car my actual dad bought with my mom.'"

A soft laugh left her lips at that. "Yeah, I can see that…" she trailed off, wondering how best to ask her next question. "Why…why did you stop talkin' to him, then?"

Dean sighed heavily. "Figured you were gonna say that."

"Sorry, we don't—"

"Nah, seems like confession time anyway," he chuckled humorlessly. By this point, they were at Crowley's, and he pulled into the lot. He put the car into park and shut off the engine, but didn't move to leave the car.

Y/N nuzzled more into Dean's side, trying not to rush him.

"It was 'cause of Crowley, actually," he finally began. "Or…I guess it's the same reason I'm here."

She reached up and took the hand that was hanging off of her shoulders and squeezed it.

He smiled before continuing. "I practically raised Sammy, you have to understand. When we weren't with Bobby, it was all up to me. Take care of Sammy, that was my job. So…so we grew up and Sammy started talkin' 'bout law school and all these amazing things he was gonna do and, damn it, he was so smart. Smartest guy you've ever met, y'know?"

His green eyes gleamed as he talked about his brother, and he became more animated than he'd been all morning.

Then he was dark once more. "Then he got sick. _Real_ sick."

"But…but he's okay. As everyone tells me, he's getting married soon," she tried to inject a modicum of humor, try to lighten the mood.

It didn't work.

"Yeah, he is now but he wasn't gonna be," he spoke slowly, like the words actually hurt him physically. "I don't really understand what was wrong, but it was something with his heart I think. The only thing that could save him was an operation...an operation we couldn't afford."

"Oh, Dean…" she leaned up, kissing the corner of his lips. "I'm so sorry."

"I'm not," he answered without a shred of hesitation in his voice. "I'd do it again in a heartbeat. What was I supposed to do? I…" he choked. "I had one job, okay? One. Job. I had to protect him, I had to—"

She pulled out of his embrace solely to rearrange herself and hold him close. He buried his face in the crook of her neck, holding her tight enough to practically strangle her, and she held him just as tight.

It was quite some time before they made it into the club.


	24. Chapter 22

When they finally walked into the club, Benny’s eyes refused to leave Dean. It was an indecipherable look to Y/N.

But the pianist seemed to understand.

At the end of their apparently silent conversation, Dean tightened his hold on her, pulling her into his side. “I need to go.”

She gulped, nodding quietly. “I’ll be here.”

He seemed reticent to go and Benny, God bless him, wasn’t rushing either.

Finally, Y/N reached up, cupping both his cheeks with her hands and pulling him down into a soft, sweet kiss. “You are one of the best men I’ve ever known.”

He answered in a barely audible and shuddery breath. “I love you.”

“I love you too,” she promised.

With one more deep breath, he left.

Benny patted Dean on the shoulder when he was close enough and sent an apologetic look to the singer. She returned it.

When they left her sight, she turned back into the club.

“Heya, girlie!”

Her attention turned to Meg, who was standing with another waitress. Meg patted the new girl on the shoulder, telling her quickly to finish cleaning all the tables, before running over to join her friend.

Y/N smiled half-heartedly. “Morning, Meg.”

“Okay, what’s wrong?”

The singer scoffed. “What’re ya, a mind reader?”

“I’m not an idiot.”

Y/N laughed at that. “Fair enough. Just been a long morning.”

Meg wiggled her eyebrow. “I’ll bet. You two are insatisiable.”

Red filled the performer’s cheeks.

Meg shrugged. “Can’t talk too much, though. Once I got choir boy to see things my way…” she trailed off, humming in contentment. “Well, let’s just say I’ve sufficiently corrupted him.”

“I’m guessin’ he doesn’t mind that.”

“Nope,” she answered, popping the p sound.

The girls laughed, making themselves at home at the bar. “Speakin’ of,” Y/N looked around. “Where is Cas?”

“Hidin’ in the back, inventorying,” Meg ran a hand through her hair. She placed her hands on the bar, putting nearly her full weight on them.

“I’m sure his favorite bit,” Y/N teased.

“It will be when I go back and join him,” Meg winked.

Y/N gasped, a little take aback. “Wh–You two– _here_?!”

The waitress pushed herself off the bar. “Y/N, I’m gonna give you some advice, one girl to another.

“One, men don’t care where you are when you got their cock in their mouth.”

If they had been drinking, Y/N would’ve spit hers across the bar.

“Two,” Meg continued on as though her friend wasn’t choking on air next to her. “We’ve sold ourselves and we need to grab what happiness we can, because we don’t know when the debt’s gonna be cashed in.”

Y/N watched her friend become a little smaller, a little less than the usual boisterous woman she’d come to love. She frowned, staring at the bar, as though that would give her the right words to say.

Meg scoffed. “I can hear you, you know?”

“I didn’t–”

“Didn’t have to. No one talks about what we did, how stupid we are. Well, I imagine Dean-o opened his heart after you opened your legs.”

“You make it sound like a transaction.”

“Didn’t mean to.”

“I know.”

Silence fell over them. “You wanna know, just ask.” Meg spoke just loud enough to be heard.

“Do you wanna tell me?”

“I dunno, honestly.”

“Have you told anyone?”

“…Castiel he…He got it out of me. Hell, he just turned those big blues on me and it came out. He knew some of it already.”

“How much?”

“Well…Castiel was already working for Crowley when I got mixed up in all this. He and Dean have been here longer than anybody. But, basically, there was a turf war and I picked the wrong side. Castiel saw the fighting up close.”

“You two were fighting? Like…Literally?”

Meg nodded. “Castiel used to be in the army. He’s a soldier. And so was I. Difference is that I was on the losing side.”

Y/N shook her head. “So you’re a POW?”

Meg laughed hollowly. “Not a bad comparison.”

The singer walked around to the other side of the bar, back where she rarely went, to stand beside her friend. “Where you telling me this?”

There was a long beat before Meg answered. “You’ve been here for months now. You’re part of this little fucked up family. We shouldn’t keep secrets, I guess.”

Y/N’s throat tightened, but Meg just continued. “Or maybe I just needed you to know because I’m selfish.”

Y/N nudged Meg’s shoulder with her own. “You wanna talk selfish?”

“What, you gotta better story than a gang war?”

The singer laughed. “You don’t know.”

Meg shrugged. “You’re right, I don’t.”

And so Y/N told her.


	25. Chapter 23

**Notes for the Chapter:**

> Hey guys! Sorry I missed last week! As y’all probably haven't heard (unless you're keeping up with my tumblr), I contracted tendinitis in my wrist, which means I can’t write as much as I want to. And then with my GIF blurbs, I’ve been a little distracted. That being said, I’m going to have to be lame and, for the foreseeable future, post every other Sunday rather than every Sunday. I promise, though, I’ll go back to my usual posting schedule once my wrist gets better, but it’ll probably be at least another three weeks before I even get an update on my condition. I’m so sorry guys, but I hope you enjoy this chapter!

Meg was impressed. She hadn’t believed her at first, but, eventually, had laughed and accepted it.

When Cas joined them soon after Y/N’s story, the waitress didn’t say a word about their conversation, instead greeting him with a kiss and commenting on how nice it was to see him.

“You saw me earlier,” he answered, his brow furrowing.

She rolled her eyes. “Let me be romantic for once, Cas.”

He nodded slowly, his clear blue eyes not leaving her.

Y/N laughed and began backing away from the couple. “I’ll leave you two lovebirds alone. I gotta get ready anyway.”

“Not so much fun to be on the other end of this, is it?” Meg teased.

“Wait until Dean gets back, and I’ll have my revenge!” the singer shouted behind her as she walked into the back.

* * *

It took another hour for Dean to return. In preparation, Y/N had gotten the small first aid kit ready and had even dragged Benny into the back to take care of him as well. The pianist had grumbled a bit about having to share his nurse, but was quickly silenced with a peck to his lips.

Benny ribbed Dean for being henpecked, but the latter told the former to shut his face, which just made Benny laugh harder.

Now that all three were in the back room, she pulled up two chairs, sitting Dean down across from her. She apologized to the bouncer for not having an extra chair, but he waved her off. The two boys chatted as Y/N worked on Dean’s wounds first (at Benny’s insistence. His exact words were “You gotta live with the man, doll. You take care of me first, you’ll never hear the end of it!”).

Not surprisingly, Dean’s knuckles were scratched up and bleeding. There was even a bruise blooming on his left cheek, though it looked minor, thankfully.

She focused on her task, not really listening to their idle chatter and teasing back and forth.

Finally, Y/N ran her fingers through Dean’s hair, petting him slightly. “You’re all set.”

“Thanks, doll,” he gave her that grin that only he could pull off. His freshly bandaged hand tangled into the small hairs at the base of her neck, pulling her into a kiss.

She pulled away too quickly for either of their liking, but she had not forgotten their guest. “Alright, Benny, you’re up!”

Dean patted his friend on the shoulder as they switched places.

Benny was in worse shape. Whereas Dean had a bruise and bleeding knuckles, Benny sported the same wounds, along with a slew of others. His arms were littered with scratches, criss-crossing a thousand similar scars. His face wasn’t too beat up, but his lip was split. He had obviously taken the brunt of the damage in the fight.

She began with wrapping his arms. Without thinking too much on it, she asked, “Is it always this bad for you?”

The boys immediately fell silent. She felt as if she had broken some code by asking about it, like this room was safe from their real world responsibilities, and she’d opened the door wide for them to return.

After a moment, Benny answered with a shrug. “You should see the other guy.”

She refrained from asking about the “other guy’s” current condition. “I can’t believe he makes you do this. Are these all from…from here?”

Benny laughed, which she didn’t expect. “Hell no. This guy was feisty today. Usually it ain’t this bad. The scars are from a long time ago.”

“From before?”

He nodded.

“What’d you do to get them?”

“No offense to you, doll,” Benny shook his head. “But I’d rather not talk about it.”

“No, of course, I’m sorry, I didn’t--”

“Don’t worry about it,” the bouncer smiled. “You’re a curious girl.” He then turned to Dean. “You better keep an eye on your girl, Dean. She’s gonna get into trouble one day.”

She tried not to react to that. There was no way that he knew what she was up to. He’d always been with Dean or at the door, nowhere near her, whenever her deal with Agent Singer had been brought up.

Dean didn’t react too much either, but she could still see him stiffen out of the corner of her eyes. And, if she could see it, so could Benny.

“I’ll keep an eye on her,” Dean tried to lighten the mood again, back to its previous height.

Benny nodded. “I just worry that she’ll do something stupid.”

“I’m right here.”

“Even if she does, you know it’ll be for the right reasons,” Dean continued on.

Benny’s eyes fell to the floor. “A lotta us do stupid shit for the right reasons. Doesn’t mean we should do them.”

“Stop talking,” Y/N said softly, partly to silence them, but partly to take a look at Benny’s lip.

A corner of his lips twitched up, but he did as asked.

They were silent as Y/N dabbed a cotton swab of hydrogen peroxide on his lips lightly, trying not to hurt him too much.

Finally, she pulled back. “All done, Benny.”

The bouncer thanked her, his Southern drawl making her feel like a real lady of leisure as he said it. Benny stood then, patting Dean on the shoulder as he headed for the door.

“If you’re doing something stupid for the right reasons,” Dean began suddenly, causing Benny to stop in his tracks. “It might be worth doing, even if it blows up in our face.”

Benny hadn’t turned around to face them, his hand still on the doorknob mid-twist. “Maybe…” he acquiesced. “You’re right. And maybe some of us aren’t brave enough to try anyway.”

Then he threw the door open and was gone.

“Does he know?” Y/N finally asked after a moment.

“Somehow, yeah,” Dean sighed heavily, running a hand over his face.

“If we got Benny to help us…” she thought aloud. “It corroborates your testimony about the…” she took his hand in hers as she searched for words.

“He won’t help us.”

“We have to try, Dean. Benny knows things. More than any of us, probably. He’s probably been to meetings to scare whoever Crowley’s negotiating with!”

“And he won’t help us.”

“We don’t know that!”

“He just said so, sweetheart,” Dean growled, getting a bit frustrated.

She squeezed his hand in both of hers, but lightly, unsure of what else to do.

Dean leaned over and pressed a kiss to her temple. “Let’s get through tonight, then we’ll talk about it at home, okay?”

She looked up into his emerald green eyes and nodded slightly. The argument wasn’t over, but the show must go on.


	26. Chapter 24

**Notes for the Chapter:**

> So, I’m FINALLY back to my baby. Hopefully the writer’s block will not fight me so much on this. I’d appreciate it. Sorry to make y’all wait so long between chapters, and I wish I could do more to apologize! D:

The show went on as usual that night.

The band played their usual set, Cas served his usual drinks, and Meg fended off more than one unwanted advance by more than one patron. Even Benny went about his usual routine, which of course meant he wasn't seen by any of his coworkers until closing time.

The singer, however, had not forgotten her earlier conversation with the muscle of Crowley's club. In fact, it was all she spoke of when she returned home that night with her pianist.

Dean tried to talk her out of it, tried to explain to her that Benny rarely changed his mind and perhaps his debt was too much for him to bear without Crowley's help.

She, in turn, tried to convince her beau that it wasn't hopeless. She argued that her own charges loomed above them, yet that hadn’t stopped her.

That argument hadn't helped her case, however. All that had done was make Dean angrier.

She could see that he had a defense for his friend on the tip of his tongue, and he was almost physically holding himself back.

She begged to understand, begged to know what was so much worse that Benny was now inextricable from Crowley.

Dean couldn’t answer.

When they finally went to bed, they hugged their respective edges of the mattress instead of each other.

They didn’t speak as they woke from fitful rests.

They didn’t speak as they readied for the day.

They didn’t speak as they drove to the club.

The first time Dean touched Y/N since their argument, it was to steer her away from the bouncer. The first time she heard his voice was when he apologized to Benny, saying that they were needed inside and he’d talk to him later.

She didn’t fight Dean as he gently guided her away from their Southern friend, but she frowned up at the pianist to let him know of her displeasure.

He answered with a tight smile. Her message was received.

The entire day, however, she was not alone again. Not because Dean was at her side any more than usual, but just because of circumstance. It was as if everyone at the club got the secret message to keep her away from Benny. She chalked it up to the fact that everyone was just as busy as usual getting things together for that evening rather than a secret plot to keep the two apart.

She ended up spending most of her time with Meg, helping her set up for the evening in exchange for her hair and make-up services before the performance that evening.

The performance began as usual. Y/N crooned into the microphone as her eyes drifted across the dark sea in front of her. Every night, she could only pick out a few faces, the guests mostly shadows in front of her, which she always assumed was on purpose.

The shadows ebbed and flowed like tides of the ocean. Throughout the evening, she caught the gaze of one of her friends as they went around doing their usual thing, but the mass as a whole remained formless, shapeless.

Finally, she got to her break. She thanked the audience before the boys played her off as she headed backstage.

Meg was already in the hallway, holding a glass of water out for the singer.

“You’re a lifesaver.”

“I try,” the waitress smirked, handing over the glass.

Y/N downed it in two gulps, then handed it back.

“Lemme touch you up a bit before you go back out there.”

The girls disappeared into the back, where Meg spent a few minutes sprucing up the singer. Then she was left alone to enjoy the last few minutes of her break.

A knock came to the door after a minute or two, and Y/N asked who it was.

A Southern drawl answered her, and she allowed him entrance.

Benny entered with a wide smile that didn’t quite reach his eyes. He closed the door behind him, then leaned against it, effectively cutting off the only exit.

Y/N sat up a little straighter in her chair, her eyes narrowing at the behavior. Her throat became dry, but she still was able to speak. “Hi-de-ho, Benny. What can I do for ya?”

Benny’s clear blue eyes fell to the floor. “This ain’t about me, sug.”

The singer nodded. “Didn’t think so.”

“The thing is, I like you,” he began. “You can sing, you fit in well enough, and you make Dean happy.”

She flushed a bit. “Most of the time.”

“Most of the time,” Benny nodded, a huff of genuine laughter leaving him.

They were silent for a moment, and then she couldn’t bear it anymore. “…but?”

Benny’s head dropped, but his eyes stayed fixed on her. His shoulders fell a bit, but he still cut an intimidating figure, even as the sadness emanated off of him. “But I can’t just stand around and watch you ruin Dean’s life.”

Y/N’s gaze fell to the floor. “I’m not trying to.”

“Oh, believe me, doll,” Benny laughed again, but there was no mirth behind it. “I know what you’re trying to do.”

“How’d you find out?”

He shrugged. “Wasn’t sure until last time we talked. Heard whispers, saw you actin’ suspicious. Hell, probably took me longer to figure it out ‘cause you were so damn scared of the feds when they came in. But I bet you got over that right quick.”

She couldn’t answer.

Look,” He sighed heavily. “I get it. But it’s gotta be over now. Please don’t make an appointment with me.”

Her eyes snapped up to his, her throat feeling like the Sahara in that moment. “Benny, please.”

“I can’t go against Crowley. You know that.”

“But you could!” She stood, her excitement getting the best of her. “My charges aren’t squat to the feds as long as we help them, and if you come forward, you  _ must _ know things Dean an’ I don’t! At the very least, you can back Dean up on the beatings!”

“My charges  _ will  _ matter to any flatfoot worth his salt, sweetheart.”

“It can’t be that bad, Benny,” she pleaded. “I mean, I robbed a bank! If you—”

“I killed someone.”

The confession hit her like a ton of bricks.

Benny wasn’t looking at her anymore. “That’s a lie. I killed a lot of people. Feds can’t overlook that. Without Crowley, I’m back in prison. You know what that’s like. I…I can’t do it.” He pushed himself off the wall, reaching behind him to grab the doorknob. “So you either stop this, or Crowley’s making you an appointment with me.”

She remembered Crowley’s threat. She knew what would happen if she was caught.

Benny opened the door, standing in the jamb and clearly fighting to come up with more words to say. “Dean’s my brother; I won’t squeal, doll.” With that, she was alone in the dressing room once more.

Her heart was nearly pounding out of her chest, and she fell back into her chair. She couldn’t breathe, couldn’t think, and certainly couldn’t stand.

Another knock came to the door, and she shrieked in response.

“Jeepers!” came the low voice of Meg from the other side of the door. As it opened, the waitress spoke. “You tryin’ to give a girl a heart attack?!”

But one look at the singer, and Meg’s ire was gone.

The waitress shut the door behind her, rushing in to figure out what was wrong.

Y/N tried to wave her off as best she could, claiming that she was fine, that everything was fine. Meg ran out and back quickly with a glass of water, telling the visibly shaken girl to drink up.

When she had calmed down enough, Meg asked, “Are you okay to go on?”

Y/N nodded. “I’ve already taken too long, I’ve gotta go.”

Meg frowned, but let her friend go. She knew that her break had gone on long enough, and they ran the risk of bringing Crowley’s wrath down upon them if they waited any longer.

Y/N squeezed Meg’s hand as they walked to the door leading back out. The singer turned to her friend and said, “Make me a promise?”

“Sure, what?”

“Make sure Cas has a shot of whiskey waiting for me after the set tonight.”

**Author's Note:**

> SHAMELESS PLUG: Also available on my tumblr!  
> http://quiddy-writes.tumblr.com/tagged/gty


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